4-[(Pyrrolidin-1-yl)methyl]-3-(trifluoromethyl)aniline → 2-(4-Imidazo[4,5-b]pyridin-3-yl-2-methyl-phenyl)-N-(4-pyrrolidin-1-ylmethyl-3-trifluoromethyl-phenyl)-acetamide

HRID 1661029Notes

Reaction equation

HRID 1661029 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=O)=[C:12]([CH3:20])[CH:11]=2)[CH:2]=1.[N:21]1([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][C:28]=2[C:34]([F:37])([F:36])[F:35])[CH2:25][CH2:24][CH2:23][CH2:22]1>C(Cl)Cl.CO>[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([NH:33][C:30]3[CH:31]=[CH:32][C:27]([CH2:26][N:21]4[CH2:22][CH2:23][CH2:24][CH2:25]4)=[C:28]([C:34]([F:37])([F:35])[F:36])[CH:29]=3)=[O:19])=[C:12]([CH3:20])[CH:11]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 598642004-[(Pyrrolidin-1-yl)methyl]-3-(trifluoromethyl)anilineHCID 67021622(4-Imidazo[4,5-b]pyridin-3-yl-2-methyl-phenyl)-acetic acid

Product 1

HCID 674281952-(4-Imidazo[4,5-b]pyridin-3-yl-2-methyl-phenyl)-N-(4-pyrrolidin-1-ylmethyl-3-trifluoromethyl-phenyl)-acetamide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound is prepared as described in Example 7 but using (4-imidazo[4,5-b]pyridin-3-yl-2-methyl-phenyl)-acetic acid (Step 60.1) and 4-pyrrolidin-1-ylmethyl-3-trifluoromethyl-phenylamine (disclosed in WO2005/051366). Title compound: ES-MS: 494.2 [M+H]+; tR=3.23 min (System 1); Rf=0.15 (CH2Cl2/MeOH, 95:5+0.1% NH3aq).

Workup

  1. customThe title compound is prepared

Sources & evidence

ORD record
ord-dbdcbf27da784abead5e34c0dbfb36ec
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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