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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (1aR,3aR,5S,7aR,15aS,Z)-5-(2-(4-ethynylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yloxy)-9-methyl-N-(1-methylcyclopropylsulfonyl)-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxamide

HRID 926013
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 926013
[C:1]([C:3]1[N:4]=[C:5]([C:8]2[CH:17]=[C:16]([O:18][C@H:19]3[CH2:43][CH2:42][C@H:22]4[C:23](=[O:41])[N:24]([CH3:40])[CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH:30][C@@H:31]5[CH2:36][C@@:32]5([C:37]([OH:39])=O)[NH:33][C:34](=[O:35])[C@@H:21]4[CH2:20]3)[C:15]3[C:10](=[C:11]([CH3:46])[C:12]([O:44][CH3:45])=[CH:13][CH:14]=3)[N:9]=2)[S:6][CH:7]=1)#[CH:2].[CH3:47]CN=C=NCCCN(C)C.C[NH:59][S:60]([CH:63]1[CH2:65][CH2:64]1)(=[O:62])=[O:61].C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[C:1]([C:3]1[N:4]=[C:5]([C:8]2[CH:17]=[C:16]([O:18][C@H:19]3[CH2:43][CH2:42][C@H:22]4[C:23](=[O:41])[N:24]([CH3:40])[CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH:30][C@@H:31]5[CH2:36][C@@:32]5([C:37]([NH:59][S:60]([C:63]5([CH3:47])[CH2:65][CH2:64]5)(=[O:62])=[O:61])=[O:39])[NH:33][C:34](=[O:35])[C@@H:21]4[CH2:20]3)[C:15]3[C:10](=[C:11]([CH3:46])[C:12]([O:44][CH3:45])=[CH:13][CH:14]=3)[N:9]=2)[S:6][CH:7]=1)#[CH:2]
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Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15334537N-methylcyclopropanesulfonamideHCID 88050653(1aR,3aR,5S,7aR,15aS,Z)-5-(2-(4-ethynylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yloxy)-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylic acid

Produkt 1

HCID 88050651
(1aR,3aR,5S,7aR,15aS,Z)-5-(2-(4-ethynylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yloxy)-9-methyl-N-(1-methylcyclopropylsulfonyl)-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To compound 46 (0.00003 mmol) in DCM (2 mL) under nitrogen was added EDCI (0.000062 mmol). The reaction mixture was stirred at room temperature for 2 hrs. Methyl-cyclopropylsulfonamide (0.00012 mmol) and DBU (0.00012 mmol) were then added and the reaction was stirred at room temperature for 16 hrs. DCM was then added, the mixture was washed with water and brine. Solvent was evaporated and the crude material was purified by silica gel chromatography (DCM/MeOH) to yield compound 52 as a white solid. MS (ESI, EI+): m/z=760 (MH+).

Aufarbeitung

  1. stirringthe reaction was stirred at room temperature for 16 hrs
  2. washthe mixture was washed with water and brine
  3. customSolvent was evaporated
  4. customthe crude material was purified by silica gel chromatography (DCM/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-8f675c904444446990bdbe4c3ca96d1e
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09284307B2

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