Chloroacetyl chloride → 2-chloro-N-(2-(4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)ethyl)-N-methylacetamide

HRID 912535Notes

Reaction equation

HRID 912535 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][N:7]1[C:15]2[CH:14]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][NH:25][CH3:26])=[C:18]([C:27]([F:30])([F:29])[F:28])[CH:17]=3)[N:12]=[C:11]([C:31]#[N:32])[C:10]=2[N:9]=[CH:8]1.C(N(C(C)C)C(C)C)C>C1COCC1.C(OCC)(=O)C>[Cl:1][CH2:2][C:3]([N:25]([CH2:24][CH2:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:13]2[N:12]=[C:11]([C:31]#[N:32])[C:10]3[N:9]=[CH:8][N:7]([CH3:6])[C:15]=3[CH:14]=2)=[CH:17][C:18]=1[C:27]([F:29])([F:30])[F:28])[CH3:26])=[O:4]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 59410639HCID 59410639, compound

Product 1

HCID 594106512-chloro-N-(2-(4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)ethyl)-N-methylacetamideYield 80.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

At 0° C., 2-chloroacetyl chloride (127 mg) was added to a solution of 1-methyl-6-(4-(2-(methylamino)ethoxy)-3-(trifluoromethyl)phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile (211 mg) and N-ethyl-N-isopropylpropan-2-amine (0.465 ml) dissolved in THF (5 ml). Reaction mixture was stirred at room temperature for 1 hour. Reaction mixture diluted with ethyl acetate, washed with sodium bicarbonate and water. Organic layer was dried over magnesium sulphate, solvent removed under vacuo to afford 2-chloro-N-(2-(4-(4-cyano-1-methyl-1H-imidazo[4,5-c]pyridin-6-yl)-2-(trifluoromethyl)phenoxy)ethyl)-N-methylacetamide (205 mg). 1H NMR (CDCL3) δ: 8.22 (m, 2H), 8.08 (s, 1H), 7.87 (s, 1H), 7.13 (d, 1H), 4.32 (t, 2H), 4.13 (s, 2H), 3.99 (s, 3H), 3.88 (t, 2H), 3.29 (s, 3H). MS m/z 452.0 (M+H).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. washwashed with sodium bicarbonate and water
  4. dry with materialOrganic layer was dried over magnesium sulphate, solvent
  5. customremoved under vacuo

Sources & evidence

ORD record
ord-cb1c4a7a48494650b165205d825752f4
Source dataset
uspto-grants-2011_09
Patent number
US08026236B2

Reaction notes

Loading…