N-Methylethylamine → 6-(4-(1-(2-(dimethylamino)ethyl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-5-((ethyl(methyl)amino)methyl)pyrimidin-4-amine

HRID 2284018Notes

Reaction equation

HRID 2284018 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=O)=[C:6]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[N:17]([CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])[CH:18]=[C:19]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=4)[N:20]=3)[CH2:12][CH2:11]2)[N:5]=[CH:4][N:3]=1.[CH2:37]([NH:39][CH3:40])[CH3:38]>ClCCCl>[CH3:36][N:34]([CH3:35])[CH2:33][CH2:32][N:17]1[CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([C:28]([F:29])([F:31])[F:30])[CH:22]=2)[N:20]=[C:16]1[CH:13]1[CH2:12][CH2:11][N:10]([C:6]2[N:5]=[CH:4][N:3]=[C:2]([NH2:1])[C:7]=2[CH2:8][N:39]([CH2:37][CH3:38])[CH3:40])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 12219N-MethylethylamineHCID 894427194-Amino-6-{4-[1-(2-dimethylamino-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbaldehyde

Product 1

HCID 894427496-(4-(1-(2-(dimethylamino)ethyl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-5-((ethyl(methyl)amino)methyl)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-Amino-6-{4-[1-(2-dimethylamino-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbaldehyde (90.00 mg; 0.18 mmol; 1.00 eq.) in 1 ml DCE added ethyl-methyl-amine (0.02 ml; 0.19 mmol; 1.05 eq.) and sodium p-triacetoxyborohydride (113.20 mg; 0.53 mmol; 3.00 eq.), stirred for overnight at RT, lc-ms showed desired (<30%, major ms 618/619), purified by prep HPLC, collected title compound. LC-MS: (M+1=549, obsd.=549).

Workup

  1. custompurified by prep HPLC
  2. customcollected title compound

Sources & evidence

ORD record
ord-f68509765e194071baf5c304d83094d6
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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