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Acetic Acid → HCID 69010680, Verbindung

HRID 657409
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 657409
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:45][CH3:46])=[C:10]([CH2:19][N:20]([CH2:29][C:30]3[CH:31]=[C:32]([C:37]4[CH:42]=[CH:41][CH:40]=[C:39](C=O)[CH:38]=4)[C:33]([F:36])=[CH:34][CH:35]=3)[C:21]([C:23]3([C:26]([NH2:28])=[O:27])[CH2:25][CH2:24]3)=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[CH3:47][N:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1.[C:54](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:45][CH3:46])=[C:10]([CH2:19][N:20]([CH2:29][C:30]3[CH:31]=[C:32]([C:37]4[CH:42]=[CH:41][CH:40]=[C:39]([CH2:47][N:48]5[CH2:53][CH2:52][N:51]([CH3:54])[CH2:50][CH2:49]5)[CH:38]=4)[C:33]([F:36])=[CH:34][CH:35]=3)[C:21]([C:23]3([C:26]([NH2:28])=[O:27])[CH2:24][CH2:25]3)=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 86633359HCID 86633359, Verbindung

Produkt 1

HCID 69010680HCID 69010680, VerbindungAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

A mixture of N1-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N1-[(6-fluoro-3′-formyl-3-biphenylyl)methyl]-1,1-cyclopropanedicarboxamide (50 mg, 0.080 mmol), 1-methylpiperazine (7.99 mg, 0.080 mmol), sodium triacetoxyborohydride (33.8 mg, 0.160 mmol) and acetic acid (5.48 μL, 0.096 mmol) in DCM (3 mL) was stirred at room temperature over the weekend. The reaction mixture was quenched with saturated NaHCO3 and extracted with DCM twice. The combined organic layers were concentrated under vacuum to give the crude residue. It was purified by reverse phase hplc with a Gilson HPLC (acidic conditions: 0.1% TFA in the solvents), eluting with 10 to 70% CH3CN in water at a flow rate of 20 mL/min. The product fractions were combined, washed with saturated NaHCO3 and extracted with ethyl acetate twice. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and then concentrated under vacuum to give N1-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N1-({6-fluoro-3′-[(4-methyl-1-piperazinyl)methyl]-3-biphenylyl}methyl)-1,1-cyclopropanedicarboxamide as a solid (28 mg, 49.4%). LC-MS m/z 712 (M+H)+, 0.85 min (ret time); 1H NMR (400 MHz, DMSO-d6) δ 1.19 (t, J=7.53 Hz, 3H) 1.28-1.36 (m, 7H) 1.45-1.51 (m, 2H) 1.84-1.91 (m, 2H) 2.15 (s, 3H) 2.32-2.35 (m, 8H) 2.83 (q, J=7.53 Hz, 2H) 3.48-3.56 (m, 4H) 3.80-3.86 (m, 2H) 4.03-4.10 (m, 1H) 4.27-4.35 (m, 4H) 4.38 (d, J=6.02 Hz, 2H) 6.74 (d, J=7.78 Hz, 1H) 7.19-7.26 (m, 2H) 7.28-7.49 (m, 5H) 7.99 (s, 1H) 8.48 (t, J=5.77 Hz, 1H) 9.02 (t, J=5.77 Hz, 1H).

Aufarbeitung

  1. customThe reaction mixture was quenched with saturated NaHCO3
  2. extractionextracted with DCM twice
  3. concentrationThe combined organic layers were concentrated under vacuum
  4. customto give the crude residue
  5. customIt was purified by reverse phase hplc with a Gilson HPLC (acidic conditions
  6. wash0.1% TFA in the solvents), eluting with 10 to 70% CH3CN in water at a flow rate of 20 mL/min
  7. washwashed with saturated NaHCO3
  8. extractionextracted with ethyl acetate twice
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-77ce45ad81ea4b70b46c3615c9657838
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08071588B2

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