4-(Trifluoromethyl)benzoyl chloride → HCID 178488213, compound

HRID 897569Notes

Reaction equation

HRID 897569 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([C:9](Cl)=[O:10])=[CH:5][CH:4]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:29]3[C:24](=[N:25][CH:26]=[N:27][C:28]=3[NH2:30])[N:23]([C@H:31]3[CH2:36][CH2:35][C@H:34]([N:37]4[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]4)[CH2:33][CH2:32]3)[N:22]=2)=[CH:17][C:16]=1[O:44][CH3:45]>N1C=CC=CC=1>[NH2:30][C:28]1[N:27]=[CH:26][N:25]=[C:24]2[N:23]([C@H:31]3[CH2:36][CH2:35][C@H:34]([N:37]4[CH2:38][CH2:39][N:40]([CH3:43])[CH2:41][CH2:42]4)[CH2:33][CH2:32]3)[N:22]=[C:21]([C:18]3[CH:19]=[CH:20][C:15]([NH:14][C:9](=[O:10])[C:6]4[CH:7]=[CH:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=4)=[C:16]([O:44][CH3:45])[CH:17]=3)[C:29]=12

Participants

4

Reactant 2

HCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 178488198HCID 178488198, compound

Product 1

HCID 178488213HCID 178488213, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-(Trifluoromethyl)-1-benzenecarbonyl chloride (262 mg, 1.256 mmol) in dichloromathane (1 mL) was added to a solution of trans-3-(4-amino-3-methoxyphenyl)-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (500 mg, 1.145 mmol) in pyridine (8 mL) at 0° C. After 30 minutes, the ice bath was removed the the reaction mixture was stirred at room temperature for 1.5 hour. Solvent was evaporated and the residue was purified by flash column chromatography using dichloromethane/methanol (80:20) as mobile phase to give trans-N1-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-4-(trifluoromethyl)benzamide (516 mg, 74%). 1H NMR (CDCl3-d) δ 1.55 (m, 2H), 1.74 (m, 2H), 2.10-2.27 (m, 6H), 2.30 (s, 3H), 2.51 (m, 4H), 2.66 (m, 3H), 3.96 (s, 3H), 4.04 (s, 3H), 4.78 (m, 1H), 5.57 (bs, 2H), 7.30 (m, 2H), 7.79 (d, J=8.25 Hz, 2H), 8.04 (d, J=8.05 Hz, 2H), 8.38 (s, 1H), 8.64 (s, 1H), 8.68 (d, J=8.20 Hz, 1H).

Workup

  1. customthe ice bath was removed the the reaction mixture
  2. customSolvent was evaporated
  3. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-60640deb60a344ee99122aa8e76bc961
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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