Tetrahydrofuran → HCID 178433991, compound

HRID 433939Notes

Reaction equation

HRID 433939 reaction equation
Cl[C:2]1[C:7]([C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([C:21]([F:24])([F:23])[F:22])[CH:15]=2)=[O:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:25]([CH3:29])[N:26]=[C:27]([CH3:28])[C:3]=12.C1C[O:33]CC1>C(N(CC)C(C)C)(C)C.O>[F:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:11]([NH:10][C:8]([C:7]2[C:2]([OH:33])=[C:3]3[C:27]([CH3:28])=[N:26][N:25]([CH3:29])[C:4]3=[N:5][CH:6]=2)=[O:9])=[O:12])=[CH:15][C:16]=1[C:21]([F:24])([F:23])[F:22]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 23593670HCID 23593670, compound

Product 1

HCID 178433991HCID 178433991, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A suspension of (4-chloro-1,3-dimethylpyrazolo[5,4-b]pyridin-5-yl)-N-({[4-fluoro-3-(trifluoromethyl)phenyl]amino}carbonyl)carboxamide (0.050 g) in THF (5 mL) was dissolved in a 1:3 mixture of N,N-diisopropylethylamine (DIPEA) and water (4 mL). The solution was stirred at room temperature for 24 h, concentrated, and the residue purified by column chromatography on silica-gel eluting with 3:1 EtOAc-MeOH to give the title compound as a white powder. 1H NMR (DMSO-d6) δ 2.46 (s, 3H), 3.75 (s, 3H), 7.45 (dd, J=9.9, 9.9 Hz, 1H), 7.81 (m, 1H), 8.11 (dd, J=6.6, 2.6 Hz, 1H), 8.58 (s, 1H), 11.51 (br s, 1H). MS (ESI) m/z 410.

Workup

  1. concentrationconcentrated
  2. customthe residue purified by column chromatography on silica-gel
  3. washeluting with 3:1 EtOAc-MeOH

Sources & evidence

ORD record
ord-a8a22512ea5d46c88390e19e6b5f09ed
Source dataset
uspto-grants-2003_12
Patent number
US06670364B2

Reaction notes

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