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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → (11S,11aS)-allyl 7-methoxy-8-(4-((5-((4-(5-(methoxycarbonyl)-1-methyl-1H-pyrrol-3-yl)phenyl)carbamoyl)-1-methyl-1H-pyrrol-3-yl)amino)-4-oxobutoxy)-5-oxo-11-((tetrahydro-2H-pyran-2-yl)oxy)-2,3,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10(5H)-carboxylate

HRID 2207469
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2207469
[CH2:1]([O:4][C:5]([N:7]1[C:13]2[CH:14]=[C:15]([O:20][CH2:21][CH2:22][CH2:23][C:24]([NH:26][C:27]3[CH:28]=[C:29]([C:33]([OH:35])=O)[N:30]([CH3:32])[CH:31]=3)=[O:25])[C:16]([O:18][CH3:19])=[CH:17][C:12]=2[C:11](=[O:36])[N:10]2[CH2:37][CH2:38][CH2:39][C@H:9]2[C@@H:8]1[O:40][CH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][O:42]1)=[O:6])[CH:2]=[CH2:3].CCN=C=NCCCN(C)C.Cl.C(OC(N1C2C=C(OCCCC(O)=O)C(OC)=CC=2C(=O)N2CCCC2C1OC1CCCCO1)=O)C=C.[NH2:96][C:97]1[CH:102]=[CH:101][C:100]([C:103]2[CH:104]=[C:105]([C:109]([O:111][CH3:112])=[O:110])[N:106]([CH3:108])[CH:107]=2)=[CH:99][CH:98]=1>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:19][O:18][C:16]1[C:15]([O:20][CH2:21][CH2:22][CH2:23][C:24]([NH:26][C:27]2[CH:28]=[C:29]([C:33](=[O:35])[NH:96][C:97]3[CH:102]=[CH:101][C:100]([C:103]4[CH:104]=[C:105]([C:109]([O:111][CH3:112])=[O:110])[N:106]([CH3:108])[CH:107]=4)=[CH:99][CH:98]=3)[N:30]([CH3:32])[CH:31]=2)=[O:25])=[CH:14][C:13]2[N:7]([C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[C@@H:8]([O:40][CH:41]3[CH2:46][CH2:45][CH2:44][CH2:43][O:42]3)[C@@H:9]3[CH2:39][CH2:38][CH2:37][N:10]3[C:11](=[O:36])[C:12]=2[CH:17]=1
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Komponenten

7

Edukt 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58326676Methyl 4-(4-aminophenyl)-1-methyl-1H-pyrrole-2-carboxylateHCID 732365854-(10-(allyloxycarbonyl)-7-methoxy-5-oxo-11-(tetrahydro-2H-pyran-2-yloxy)-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-8-yloxy)butanoic acidHCID 118061220
4-(4-(((11S,11aS)-10-((allyloxy)carbonyl)-7-methoxy-5-oxo-11-((tetrahydro-2H-pyran-2-yl)oxy)-2,3,5,10,11,11a-hexahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yl)oxy)butanamido)-1-methyl-1H-pyrrole-2-carboxylic acid

Produkt 1

HCID 131735922(11S,11aS)-allyl 7-methoxy-8-(4-((5-((4-(5-(methoxycarbonyl)-1-methyl-1H-pyrrol-3-yl)phenyl)carbamoyl)-1-methyl-1H-pyrrol-3-yl)amino)-4-oxobutoxy)-5-oxo-11-((tetrahydro-2H-pyran-2-yl)oxy)-2,3,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10(5H)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of Alloc-THP protected PBD-Py acid 14a (150 mg, 0.23 mmol, 1.0 equivalent) was dissolved in DMF. EDCl (2.49 g, 13.02 mmol, 2.0 eq) and DMAP (1.989 g, 16.28 mmol, 2.5 eq) were added to the stirred solution of 13 at room temperature and the mixture was allowed to stir for 30 minutes after which the MPB-ester 7 (67.83 mg, 0.29 mmol, 1.25 eq) was added. The reaction mixture was allowed to stir for a further 3 hour at which point TLC showed completion of reaction. The reaction was quenched by pouring it onto a mixture of ice/water mixture and the resulting mixture was extracted with ethyl acetate (3×150 mL). The combined extracts were sequentially washed with citric acid (50 mL), saturated aqueous NaHCO3 (50 mL), water (50 mL), brine (50 mL) and finally dried over MgSO4. Excess ethyl acetate was evaporated by rotary evaporator under reduced pressure and the crude product was directly used in the next step without further purification. m/z (+EI) calc. for C45H52N6O11 (M)+ 852.93. found 854.87 ([M+H]+.

Aufarbeitung

  1. additionwas added
  2. customcompletion of reaction
  3. customThe reaction was quenched
  4. additionby pouring it
  5. additiononto a mixture of ice/water mixture
  6. extractionthe resulting mixture was extracted with ethyl acetate (3×150 mL)
  7. washThe combined extracts were sequentially washed with citric acid (50 mL), saturated aqueous NaHCO3 (50 mL), water (50 mL), brine (50 mL)
  8. dry with materialfinally dried over MgSO4
  9. customExcess ethyl acetate was evaporated by rotary evaporator under reduced pressure
  10. customthe crude product was directly used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-1801350adb164cad916a49341c839b8b
Quelldatensatz
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09376440B2

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