HCID 71280376, compound → Ammonia

HRID 2401126Notes

Reaction equation

HRID 2401126 reaction equation
C([O:3][C:4]([C:6]1([CH2:30][CH2:31][NH:32][C:33]2[C:34]([CH3:50])=[N:35][C:36]([N:39]3[CH2:43][CH2:42][C@@H:41]([N:44]4[CH2:48][CH2:47][CH2:46][C@@H:45]4[CH3:49])[CH2:40]3)=[CH:37][CH:38]=2)[CH2:11][CH2:10][CH:9]([O:12][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][CH2:7]1)=O)C>CO.C(Cl)Cl>[C:26]([Si:13]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[O:12][CH:9]1[CH2:8][CH2:7][C:6]2([C:4](=[O:3])[N:32]([C:33]3[C:34]([CH3:50])=[N:35][C:36]([N:39]4[CH2:43][CH2:42][C@@H:41]([N:44]5[CH2:48][CH2:47][CH2:46][C@@H:45]5[CH3:49])[CH2:40]4)=[CH:37][CH:38]=3)[CH2:31][CH2:30]2)[CH2:11][CH2:10]1)([CH3:29])([CH3:28])[CH3:27].[NH3:32]

Participants

4

Reactant 1

HCID 71280376HCID 71280376, compound

Product 2

HCID 222AmmoniaYield 5%HCID 71280567HCID 71280567, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was synthesized in essentially the same manner using the procedures as set forth in Step 2 of Example 1, by cyclizing 4-(tert-butyl-diphenyl-silanyloxy)-1-{2-[2-methyl-6-((2S,3′R)-2-methyl-[1,3′]bipyrrolidinyl-1′-yl)-pyridin-3-ylamino]-ethyl}-cyclohexanecarboxylic acid ethyl ester (132 mg, 0.19 mmol) to obtain 89 mg (72% over two steps) of the title compound after flash column chromatography (5% 7N NH3 in MeOH/CH2Cl2).

Workup

  1. customThe title compound was synthesized in essentially the same manner

Sources & evidence

ORD record
ord-6bbb1b9f5a6a40bc8d1edc2ae78d0702
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

Loading…