6-Chloropurine → 1-(4-Chloro-3-trifluoromethylphenyl)-3-[2-(9H-purin-6-ylamino)-benzothiazol-6-yl]urea

HRID 2108923Notes

Reaction equation

HRID 2108923 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.[NH2:11][C:12]1[S:13][C:14]2[CH:20]=[C:19]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([C:32]([F:35])([F:34])[F:33])[CH:26]=3)=[O:23])[CH:18]=[CH:17][C:15]=2[N:16]=1>>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([NH:24][C:22]([NH:21][C:19]2[CH:18]=[CH:17][C:15]3[N:16]=[C:12]([NH:11][C:2]4[N:10]=[CH:9][N:8]=[C:7]5[C:3]=4[N:4]=[CH:5][NH:6]5)[S:13][C:14]=3[CH:20]=2)=[O:23])=[CH:26][C:27]=1[C:32]([F:34])([F:33])[F:35]

Participants

3

Reactant 2

HCID 53592776-ChloropurineHCID 231325021-(2-Aminobenzothiazol-6-yl)-3-(4-chloro-3-trifluoromethylphenyl)urea2×

Product 1

HCID 1785220741-(4-Chloro-3-trifluoromethylphenyl)-3-[2-(9H-purin-6-ylamino)-benzothiazol-6-yl]urea

Procedure

1-(4-Chloro-3-trifluoromethylphenyl)-3-[2-(9H-purin-6-ylamino)-benzothiazol-6-yl]urea was prepared from 6-chloropurine (17 mg, 0.11 mmol) and 1-(2-aminobenzothiazol-6-yl)-3-(4-chloro-3-trifluoromethylphenyl)urea (Intermediate 3, 42.5 mg, 0.11 mmol) according to GP 1. The reaction mixture was purified by pTLC (dichloromethane:methanol=9:1) to yield a yellow solid (35.4 mg, 70 μmol, 64%). LC/ESI-MS: m/z=505 [M(35Cl)+H]+; m/z=503 [M(35Cl)−H]−; Rt=3.87 min.

Workup

  1. customThe reaction mixture was purified by pTLC (dichloromethane:methanol=9:1)

Sources & evidence

ORD record
ord-22ec141419cb4057803f986974631b1f
Source dataset
uspto-grants-2009_04
Patent number
US07514460B2

Reaction notes

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