3-(Trifluoromethyl)benzoyl chloride → HCID 45381213, compound

HRID 2365768Notes

Reaction equation

HRID 2365768 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[N:14][C:15]=3[NH2:17])[N:10]([C@@H:18]3[CH2:22][CH2:21][O:20][CH2:19]3)[N:9]=2)=[CH:4][CH:3]=1.[F:23][C:24]([F:35])([F:34])[C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](Cl)=[O:29]>C(Cl)Cl>[NH2:17][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[N:10]([C@@H:18]3[CH2:22][CH2:21][O:20][CH2:19]3)[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:28](=[O:29])[C:27]4[CH:31]=[CH:32][CH:33]=[C:25]([C:24]([F:23])([F:34])[F:35])[CH:26]=4)=[CH:3][CH:4]=3)[C:16]=12

Participants

4

Reactant 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 58506762HCID 58506762, compound

Product 1

HCID 45381213HCID 45381213, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-(4-aminophenyl)-1-((R)-tetrahydrofuran-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.075 g, 0.25 mmol) in CH2Cl2 (10 mL) was cooled in an ice-water bath. To this, 3-(trifluoromethyl)benzoyl chloride (0.035 mL, 0.25 mmol) diluted in CH2Cl2 (5 mL) was added dropwise. The reaction was allowed to warm to room temperature and left stirring for 12 hours. The reaction proceeded until completion as judged by TLC and LC-MS, was concentrated in vacuo, resuspended in 50:50 H2O—CH3CN, and purified on a C18 column in CH3CN/H2O/0.1% TFA (1-100% gradient) to afford AD68. ESI-MS m/z [M+H]+ found 469.4, calculated 469.2.

Workup

  1. additionwas added dropwise
  2. waitleft
  3. concentrationwas concentrated in vacuo
  4. custompurified on a C18 column in CH3CN/H2O/0.1% TFA (1-100% gradient)
  5. customto afford AD68

Sources & evidence

ORD record
ord-ff7686d637504364bed5f49f18397366
Source dataset
uspto-grants-2014_04
Patent number
US08697709B2

Reaction notes

Loading…