1-{2-[2-methyl-6-((2S,3'R)-2-methyl-[1,3']bipyrrolidinyl-1'-yl)-pyridin-3-ylamino]-ethyl}-cyclohexanecarboxylic acid methyl ester → Ammonia

HRID 2401129Notes

Reaction equation

HRID 2401129 reaction equation
CO[C:3]([C:5]1([CH2:11][CH2:12][NH:13][C:14]2[C:15]([CH3:31])=[N:16][C:17]([N:20]3[CH2:24][CH2:23][C@@H:22]([N:25]4[CH2:29][CH2:28][CH2:27][C@@H:26]4[CH3:30])[CH2:21]3)=[CH:18][CH:19]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4]>CO.C(Cl)Cl>[CH3:31][C:15]1[C:14]([N:13]2[CH2:12][CH2:11][C:5]3([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]3)[C:3]2=[O:4])=[CH:19][CH:18]=[C:17]([N:20]2[CH2:24][CH2:23][C@@H:22]([N:25]3[CH2:29][CH2:28][CH2:27][C@@H:26]3[CH3:30])[CH2:21]2)[N:16]=1.[NH3:13]

Participants

4

Reactant 1

HCID 712808731-{2-[2-methyl-6-((2S,3'R)-2-methyl-[1,3']bipyrrolidinyl-1'-yl)-pyridin-3-ylamino]-ethyl}-cyclohexanecarboxylic acid methyl ester

Product 2

HCID 222AmmoniaYield 5%HCID 54590990HCID 54590990, 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 1-{2-[2-methyl-6-((2S,3′R)-2-methyl-[1,3′]bipyrrolidinyl-1′-yl)-pyridin-3-ylamino]-ethyl}-cyclohexanecarboxylic acid methyl ester (94 mg, 0.22 mmol) to obtain 35.6 mg (41% yield 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-9e1b250046274a24b716a05ba2f1a7bf
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

Loading…