Triethylamine → 4-Amino-6-{4-[1-(2-dimethylamino-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbaldehyde

HRID 2284017Notes

Reaction equation

HRID 2284017 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.FC(F)(F)C(O)=O.[N:18]1([CH2:22][CH2:23][N:24]2[CH:28]=[C:27]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[C:31]([C:36]([F:39])([F:38])[F:37])[CH:30]=3)[N:26]=[C:25]2[CH:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH2:21]C[CH2:19]1.C(N(CC)CC)C>CC#N>[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([N:43]2[CH2:44][CH2:45][CH:40]([C:25]3[N:24]([CH2:23][CH2:22][N:18]([CH3:21])[CH3:19])[CH:28]=[C:27]([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[C:31]([C:36]([F:37])([F:38])[F:39])[CH:30]=4)[N:26]=3)[CH2:41][CH2:42]2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 842305-Pyrimidinecarboxaldehyde, 4-amino-6-chloro-HCID 894427644-[1-(2-azetidin-1-yl-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidine trifluoroacetate

Product 1

HCID 894427194-Amino-6-{4-[1-(2-dimethylamino-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidin-1-yl}-pyrimidine-5-carbaldehydeYield 56.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The reaction mixture of 4-Amino-6-chloro-pyrimidine-5-carbaldehyde (150.00 mg; 0.95 mmol; 1.00 eq.), 4-[1-(2-Azetidin-1-yl-ethyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1H-imidazol-2-yl]-piperidine trifluoroacetate (2) (594.52 mg; 0.95 mmol; 1.00 eq.) and Triethyl-amine (0.80 ml; 5.71 mmol; 6.00 eq.) in MeCN 4 ml were stirred at RT for 2 hr, lc-ms showed desired as major. Filtrate, collected white solid as 4-amino-6-(4-(1-(2-(dimethylamino)ethyl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)pyrimidine-5-carbaldehyde, 277 mg, yield 56.2%. LC-MS: (M+1=506, obsd.=506).

Workup

  1. customFiltrate, collected white solid as 4-amino-6-(4-(1-(2-(dimethylamino)ethyl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)pyrimidine-5-carbaldehyde, 277 mg, yield 56.2%

Sources & evidence

ORD record
ord-cf0c4ecfa8674933b71a7d108162af5c
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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