3-(Trifluoromethyl)benzoyl chloride → N-[3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-[1,4]oxazepan-4-yl-ethoxy)-phenyl]-3-trifluoromethyl-benzamide

HRID 1626226Notes

Reaction equation

HRID 1626226 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH2:23])[CH:10]=[CH:11][C:12]=2[O:13][CH2:14][CH2:15][N:16]2[CH2:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[CH:5][CH:4]=[N:3]1.CCN(C(C)C)C(C)C.[F:33][C:34]([F:45])([F:44])[C:35]1[CH:36]=[C:37]([CH:41]=[CH:42][CH:43]=1)[C:38](Cl)=[O:39]>CC(N(C)C)=O.CS(C)=O>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH:23][C:38](=[O:39])[C:37]3[CH:41]=[CH:42][CH:43]=[C:35]([C:34]([F:33])([F:44])[F:45])[CH:36]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH2:14][CH2:15][N:16]2[CH2:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[CH:5][CH:4]=[N:3]1

Participants

6

Reactant 3

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 81531DiisopropylethylamineHCID 58964281HCID 58964281, compound

Product 1

HCID 11670336N-[3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-[1,4]oxazepan-4-yl-ethoxy)-phenyl]-3-trifluoromethyl-benzamideYield 87%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution 3-(2-methyl-2H-pyrazol-3-yl)-4-(2-[1,4]oxazepan-4-yl-ethoxy)-phenylamine (0.07 g, 0.2215 mmol) in 2.0 mL of DMA was added DIEA (0.057 g, 0.443 mmol), followed by m-trifluoromethyl benzoyl chloride (0.056 g, 0.266 mmol), and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was diluted to 5.0 mL with DMSO and purified by RP-HPLC. The proper fractions were collected and lyophilized to afford N-[3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-[1,4]oxazepan-4-yl-ethoxy)-phenyl]-3-trifluoromethyl-benzamide as an off-white semisolid in 87% yield. LCMS m/z (%)=489 (M+H, 100). 1H NMR (400 MHz, DMSO-d6) δ: 10.5 (bs, 1H), 8.29 (s, 1H), 8.26 (d, J=7.94 Hz, 1H), 7.98 (d, J=7.83 Hz, 1H), 7.89 (dd, J=8.93 and 2.55 Hz, 1H), 7.79 (t, J=7.82 Hz, 1H), 7.72 (d, J=2.53 Hz, 1H), 7.49 (s, 1H), 7.26 (d, J=9.14 Hz, 1H), 6.31 (d, J=1.79 Hz, 1H), 4.29-4.43 (m, 2H), 3.69 (s, 3H), 3.55-3.64 (m, 5H), 3.01-3.18 (m, 5H), 1.8-2.1 (m, 2H).

Workup

  1. custompurified by RP-HPLC
  2. customThe proper fractions were collected

Sources & evidence

ORD record
ord-ebb597335a2c4386b88def4ce2a1edb4
Source dataset
uspto-grants-2014_07
Patent number
US08785441B2

Reaction notes

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