5-fluoro-1H-indazol-3-amine → [2-(2-Chloro-phenyl)-pyrido[2,3-d]pyrimidin-4-yl]-(5-fluoro-1H-indazol-3-yl)-amine

HRID 133145Notes

Reaction equation

HRID 133145 reaction equation
Cl[C:2]1[C:3]2[CH:18]=[CH:17][CH:16]=[N:15][C:4]=2[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[N:7]=1.[F:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][N:24]=[C:23]2[NH2:29]>>[Cl:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:6]1[N:7]=[C:2]([NH:29][C:23]2[C:22]3[C:26](=[CH:27][CH:28]=[C:20]([F:19])[CH:21]=3)[NH:25][N:24]=2)[C:3]2[CH:18]=[CH:17][CH:16]=[N:15][C:4]=2[N:5]=1

Participants

3

Reactant 2

HCID 43278965-fluoro-1H-indazol-3-amineHCID 219392444-Chloro-2-(2-chloro-phenyl)-pyrido(2,3-d]pyrimidine

Product 1

HCID 21939157[2-(2-Chloro-phenyl)-pyrido[2,3-d]pyrimidin-4-yl]-(5-fluoro-1H-indazol-3-yl)-amine

Procedure

Prepared from 4-Chloro-2-(2-chloro-phenyl)-pyrido[2,3-d]pyrimidine (100 mg, 0.36 mmol) and 5-Fluoro-1H-indazol-3-ylamine (108 mg, 0.72 mmol). Purification by preparative HPLC afforded the title compound as a yellow, di-TFA salt (45 mg, 22% yield). HPLC-Method A, Rt 3.00 min; 1H NMR (DMSO, 500 MHz): δ 13.0 (1H, s), 10.90(1H, bs), 9.15–9.05 (2H, m), 7.70 (1H, m), 7.60–7.30 (6H, m), 7.20 (1H, m); MS (m/z), MH+ 391.1.

Workup

  1. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-5e80d001498c419fa44ec61e98d88ccf
Source dataset
uspto-grants-2008_06
Patent number
US07390815B2

Reaction notes

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