Acetamide → (S)-1-(1-{[2-cyano-4-(2-methyl-1,3-oxazol-4-yl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

HRID 2422541Notes

Reaction equation

HRID 2422541 reaction equation
[N+:1]([C:4]1[CH:41]=[CH:40][C:7]([C:8]([O:10][C@@:11]([C:18]2[N:19]=[N:20][N:21]([CH2:23][C:24]3[CH:33]=[C:32]4[C:27]([C:28]([C:36](=O)[CH2:37]Br)=[CH:29][C:30]([C:34]#[N:35])=[N:31]4)=[CH:26][CH:25]=3)[CH:22]=2)([C:14]([F:17])([F:16])[F:15])[CH2:12][CH3:13])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:42]([NH2:45])(=[O:44])[CH3:43]>CN(C=O)C.C(OCC)(=O)C>[N+:1]([C:4]1[CH:41]=[CH:40][C:7]([C:8]([O:10][C@@:11]([C:18]2[N:19]=[N:20][N:21]([CH2:23][C:24]3[CH:33]=[C:32]4[C:27]([C:28]([C:36]5[N:45]=[C:42]([CH3:43])[O:44][CH:37]=5)=[CH:29][C:30]([C:34]#[N:35])=[N:31]4)=[CH:26][CH:25]=3)[CH:22]=2)([C:14]([F:15])([F:16])[F:17])[CH2:12][CH3:13])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 178AcetamideHCID 86621977(S)-1-(1-{[4-(bromoacetyl)-2-cyanoquinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

Product 1

HCID 66791318(S)-1-(1-{[2-cyano-4-(2-methyl-1,3-oxazol-4-yl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-1-(1-{[4-(bromoacetyl)-2-cyanoquinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate (0.16 g, 0.25 mmol) and acetamide (16 mg, 0.28 mmol) in DMF (0.25 mL) was stirred at room temperature for 4 h then at 100° C. overnight. The reaction mixture was diluted in ethyl acetate, washed with water, brine and dried over MgSO4. The crude compound was purified on silica gel (eluting solvent: 2% to 5% acetone in dichloromethane) to give the desired titled product. 1H NMR (acetone-d6): δ 8.9 (d, 1H), 8.72 (s, 1H), 8.53 (s, 1H), 8.42 (d, 2H), 8.30 (d, 2H), 8.25 (s, 1H), 8.05 (s, 1H), 7.77 (d, 1H), 6.05 (s, 2H), 3.05 (m, 1H), 2.85 (m, 1H), 2.6 (s, 3H), 1.15 (t, 3H); and also the reduced compound 1-{1-[(4-acetyl-2-cyanoquinolin-7-yl)methyl]-1H-1,2,3-triazol-4-yl}-1-(trifluoromethyl)propyl 4-nitrobenzoate. 1H NMR (acetone-d6): δ 8.55 (m, 2H), 8.45 (m, 3H), 8.3 (d, 2H), 8.07 (s, 1H), 7.82 (d, 1H), 6.05 (s, 2H), 3.05 (m, 1H), 2.85 (s, 3H), 2.82 (m, 1H), 1.12 (t, 3H).

Workup

  1. customat 100° C.
  2. customovernight
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. customThe crude compound was purified on silica gel (eluting solvent: 2% to 5% acetone in dichloromethane)

Sources & evidence

ORD record
ord-ffe1d98a91a243f48f5d7e42b327622c
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

Loading…