Pyrrolidine → 1-methyl-6-(4-(2-(1-(2-(pyrrolidin-1-yl)acetyl)piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

HRID 912541Notes

Reaction equation

HRID 912541 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:25]=[C:24]([C:26]#[N:27])[C:23]4[N:28]=[CH:29][N:30]([CH3:31])[C:22]=4[CH:21]=3)=[CH:16][C:15]=2[C:32]([F:35])([F:34])[F:33])[CH2:7][CH2:6]1)=[O:4].[CH:36]([N:39]([CH:42]([CH3:44])C)CC)([CH3:38])C.N1CCCC1>CO>[CH3:31][N:30]1[C:22]2[CH:21]=[C:20]([C:17]3[CH:18]=[CH:19][C:14]([O:13][CH2:12][CH2:11][CH:8]4[CH2:7][CH2:6][N:5]([C:3](=[O:4])[CH2:2][N:39]5[CH2:36][CH2:38][CH2:44][CH2:42]5)[CH2:10][CH2:9]4)=[C:15]([C:32]([F:34])([F:33])[F:35])[CH:16]=3)[N:25]=[C:24]([C:26]#[N:27])[C:23]=2[N:28]=[CH:29]1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 59410702HCID 59410702, compound

Product 1

HCID 468427741-methyl-6-(4-(2-(1-(2-(pyrrolidin-1-yl)acetyl)piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-(4-(2-(1-(2-chloroacetyl)piperidin-4-yl)ethoxy)-3-(trifluoromethyl)phenyl)-1-methyl-1H-imidazo[4,5-c]pyridine-4-carbonitrile (25 mg), diisopropylethylamine (82 μL), and pyrrolidine (21 μL) in MeOH (1 ml) was stirred for 36 hours at room temperature. The mixture was purified by prep HPLC (acidic) to give the expected product (14 mg). 1H NMR (CD3OD) δ: 8.42 (s, 1H), 8.24-8.35 (m, 3H), 7.27 (d, 1H), 4.50 (d, 1H), 4.23 (t, 2H), 3.91-4.07 (m, 4H), 3.22-3.61 (m, 6H), 3.05 (t, 1H), 2.64 (t, 1H), 1.76-2.02 (m, 9H), 1.10-1.30 (m, 2H). MS m/z 541 (M+H).

Workup

  1. customThe mixture was purified by prep HPLC (acidic)

Sources & evidence

ORD record
ord-ee3d0e665d054d6394e500a5f142ae12
Source dataset
uspto-grants-2011_09
Patent number
US08026236B2

Reaction notes

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