HCID 18761456, compound → N1-{4-[4-amino-1-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-3-phenylpropanamide

HRID 432286

Reaction equation

HRID 432286 reaction equation
C1(CCC(Cl)=O)C=CC=CC=1.[NH2:12][C:13]1[N:18]=[CH:17][N:16]=[C:15]2[N:19]([CH:41]3[CH2:46][CH2:45][N:44]([CH:47]4[CH2:52][CH2:51][N:50]([CH3:53])[CH2:49][CH2:48]4)[CH2:43][CH2:42]3)[N:20]=[C:21]([C:22]3[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:38])[CH2:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[C:24]([O:39][CH3:40])[CH:23]=3)[C:14]=12.NC1C=CC(C2C3C(=NC=NC=3N)N(C3CCN(C4CCN(C)CC4)CC3)N=2)=CC=1OC>N1C=CC=CC=1>[NH2:12][C:13]1[N:18]=[CH:17][N:16]=[C:15]2[N:19]([CH:41]3[CH2:46][CH2:45][N:44]([CH:47]4[CH2:48][CH2:49][N:50]([CH3:53])[CH2:51][CH2:52]4)[CH2:43][CH2:42]3)[N:20]=[C:21]([C:22]3[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:38])[CH2:30][CH2:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)=[C:24]([O:39][CH3:40])[CH:23]=3)[C:14]=12

Participants

4

Reactant 2

HCID 18761456HCID 18761456, compoundHCID 223469753-(4-amino-3-methoxyphenyl)-1-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 18761457N1-{4-[4-amino-1-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-3-phenylpropanamideYield 18%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N1-{4-[4-Amino-1-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-3-phenylpropanamide 3-Phenylpropanoyl chloride (77 mg, 0.458 mmol) was added to a solution of 3-(4-amino-3-methoxyphenyl)-1-[1-(1-methylpiperidin-4-yl)-piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (100 mg, 0.229 mmol) in pyridine (1.2 mL). After 5 hours, the solvent was evaporated and the residue was purified by flash column chromatography to give N1-{4-[4-amino-1-[1-(1-methylpiperidin-4-yl)piperidin-4-yl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-methoxyphenyl}-3-phenylpropanamide (24 mg, 18%). 1H NMR (CDCl3-d) δ 1.70 (m, 2H), 1.85 (m, 2H), 2.04 (m, 4H), 2.30 (s, 3H), 2.41 (m, 5H), 2.75 (m, 2H), 2.97 (m, 2H), 3.08 (m, 4H), 3.90 (s, 3H), 4.75 (m, 1H), 5.71 (bs, 2H), 7.24 (m, 8H), 7.76 (s, 1H), 8.34 (s, 1H), 8.52 (d, J=8.12, 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+ =569.5, Rt=1.65 min.

Workup

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

Sources & evidence

ORD record
ord-5bd0f60807bb432780c256d76dcfebe8
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Linked notes

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