Benzenepropanoyl chloride → HCID 22346959, compound

HRID 432296Notes

Reaction equation

HRID 432296 reaction equation
[C:1]1([CH2:7][CH2:8][C:9](Cl)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:27]3[C:22](=[N:23][CH:24]=[N:25][C:26]=3[NH2:28])[N:21]([CH:29]3[CH2:34][CH2:33][N:32]([CH2:35][C:36]4[NH:37][CH:38]=[CH:39][N:40]=4)[CH2:31][CH2:30]3)[N:20]=2)=[CH:15][C:14]=1[O:41][CH3:42]>N1C=CC=CC=1>[NH2:28][C:26]1[N:25]=[CH:24][N:23]=[C:22]2[N:21]([CH:29]3[CH2:34][CH2:33][N:32]([CH2:35][C:36]4[NH:37][CH:38]=[CH:39][N:40]=4)[CH2:31][CH2:30]3)[N:20]=[C:19]([C:16]3[CH:17]=[CH:18][C:13]([NH:12][C:9](=[O:10])[CH2:8][CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[C:14]([O:41][CH3:42])[CH:15]=3)[C:27]=12

Participants

4

Reactant 2

HCID 64801Benzenepropanoyl chlorideHCID 22346761HCID 22346761, compound

Product 1

HCID 22346959HCID 22346959, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Phenylpropanoyl chloride (0.011 mL, 0.0715 mmol) was added to a solution of 3-(4-amino-3-methoxyphenyl)-1-[1-(1H-2-imidazolylmethyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (30 mg, 0.0715 mmol) in pyridine (1.2 mL) at 0° C. After 2 hours, the solvent was evaporated and the residue was purified by flash column chromatography to give N1-(4-{4-amino-1-[1-(1H-2-imidazolylmethyl)-4-piperidyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-2-methoxyphenyl)-3-phenylpropanamide (20 mg, 51%). 1H NMR (CDCl3) δ 2.27 (m, 2H), 2.61 (m, 2H), 2.76 (m, 4H), 3.09 (m, 2H), 3.93 (s, 3H), 4.07 (s, 2H), 4.96 (m, 1H), 5.61 (bs, 2H), 7.06-7.33 (m, 10H), 7.78 (s, 1H), 8.35 (s, 1H), 8.55 (d, J=8.15 Hz, 1H). LCMS (Finigan-Column: Pecosphere, C18, 3 um, 33×4.6 mm. Eluents: 0% B/A to 100% B/A in 4 min. (B: acetonitrile, A: 50 mM ammonia acetate buffer, pH 4.5), 3.0 mL/min.): MH+ =552.5, Rt=1.83 min.

Workup

  1. customthe solvent was evaporated
  2. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-4ff21df1152947b69f1f771d99ef04b7
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

Loading…