Cyclopropanemethanamine → 4-Amino-6-{4-[1-[2-(cyclopropylmethyl-amino)-ethyl]-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbonitrile

HRID 2284063Notes

Reaction equation

HRID 2284063 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[N:15]([CH2:30][CH2:31]OS(C)(=O)=O)[CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[C:21]([C:26]([F:29])([F:28])[F:27])[CH:20]=4)[N:18]=3)[CH2:10][CH2:9]2)[C:3]=1[C:37]#[N:38].[CH:39]1([CH2:42][NH2:43])[CH2:41][CH2:40]1>>[NH2:1][C:2]1[C:3]([C:37]#[N:38])=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[N:15]([CH2:30][CH2:31][NH:43][CH2:42][CH:39]4[CH2:41][CH2:40]4)[CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[C:21]([C:26]([F:29])([F:28])[F:27])[CH:20]=4)[N:18]=3)[CH2:10][CH2:9]2)[N:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 75646CyclopropanemethanamineHCID 89442673Methanesulfonic acid 2-[2-[1-(6-amino-5-cyano-pyrimidin-4-yl)-piperidin-4-yl]-4-(4-fluoro-3-trifluoromethyl-phenyl)-imidazol-1-yl]-ethyl ester

Product 1

HCID 894425474-Amino-6-{4-[1-[2-(cyclopropylmethyl-amino)-ethyl]-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbonitrileYield 40.3%

Procedure

The title compound was prepared by stirring methanesulfonic acid 2-[2-[1-(6-amino-5-cyano-pyrimidin-4-yl)-piperidin-4-yl]-4-(4-fluoro-3-trifluoromethyl-phenyl)-imidazol-1-yl]-ethyl ester (85.0 mg; 0.15 mmol; 1.00 eq) in cyclopropylmethylamine (54.6 mg, 0.77 mmol; 5.0 eq) at ambient temperature. The reaction mixture was purified via flash chromatography using a gradient of 0-10% methanol in dichloromethane to give 4-Amino-6-{4-[1-[2-(cyclopropylmethyl-amino)-ethyl]-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbonitrile (32.7 mg; 0.06 mmol; 40.3%). LC-MS: (M+1=529, obsd.=529).

Workup

  1. customThe title compound was prepared
  2. customThe reaction mixture was purified via flash chromatography

Sources & evidence

ORD record
ord-f8e17c8f542f45d5a0034d17dddd9a46
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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