6-Methoxy-3-pyridinylamine → N-(2-[((3R)-1-{1-[3-(aminocarbonyl)phenyl]piperidin-4-yl)pyrrolidin-3-yl)amino]-2-oxoethyl}-3-(trifluoromethyl)benzamide

HRID 564374Notes

Reaction equation

HRID 564374 reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:19][CH2:18][C@@H:17]([NH:20][C:21](=[O:36])[CH2:22][NH:23][C:24](=[O:35])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=4)[CH2:16]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.CO[C:39]1N=CC(N)=C[CH:40]=1>>[NH2:8][C:3]([C:4]1[CH:5]=[C:6]([N:9]2[CH2:10][CH2:11][CH:12]([N:15]3[CH2:19][CH2:18][C@@H:17]([NH:20][C:21](=[O:36])[CH2:22][NH:23][C:24](=[O:35])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=4)[CH2:16]3)[CH2:13][CH2:14]2)[CH:7]=[CH:39][CH:40]=1)=[O:2]

Participants

3

Reactant 2

HCID 811216-Methoxy-3-pyridinylamineHCID 16722463N-[2-({(3R)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide

Product 1

HCID 57814098N-(2-[((3R)-1-{1-[3-(aminocarbonyl)phenyl]piperidin-4-yl)pyrrolidin-3-yl)amino]-2-oxoethyl}-3-(trifluoromethyl)benzamide

Procedure

N-(2-[((3R)-1-{1-[3-(aminocarbonyl)phenyl]piperidin-4-yl)pyrrolidin-3-yl)amino]-2-oxoethyl}-3-(trifluoromethyl)benzamide was synthesized in similar fashion to N-[2-({(3R)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide, substituting 3-aminobenzamide for 6-methoxypyridin-3-amine. The crude product was purified by preparative HPLC. MS m/z: 518 (M+1).

Workup

  1. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-af792b1c39634798bf5a8ee9c769c25d
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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