Imidazole → HCID 18183238, compound

HRID 1359453Notes

Reaction equation

[CH2:1]([O:4][C:5]([NH:7][C:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:22]([Cl:23])=[CH:21][N:20]=[C:19]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH2:32]OS(C4C=CC(C)=CC=4)(=O)=O)=[CH:27][CH:26]=3)[N:18]=2)=[CH:13][C:12]=1[F:44])([CH3:10])[CH3:9])=[O:6])[CH:2]=[CH2:3].[NH:45]1[CH:49]=[CH:48][N:47]=[CH:46]1>>[CH2:1]([O:4][C:5]([NH:7][C:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:22]([Cl:23])=[CH:21][N:20]=[C:19]([NH:24][C:25]3[CH:26]=[CH:27][C:28]([CH2:31][CH2:32][N:45]4[CH:49]=[CH:48][N:47]=[CH:46]4)=[CH:29][CH:30]=3)[N:18]=2)=[CH:13][C:12]=1[F:44])([CH3:10])[CH3:9])=[O:6])[CH:2]=[CH2:3]

Participants

Reactant 2

HCID 795Imidazole

HCID 18183245HCID 18183245, compound

Product 1

HCID 18183238HCID 18183238, compoundYield 78.1%

Procedure

The title compound was prepared from 4-[4-(1-allyloxycarbonylamino-1-methylethyl)-3-fluorophenyl]-5-chloro-N-[4-(2-p-toluenesulphonyloxyethyl)-phenyl]pyrimidine-2-amine (504 mg, 0.79 mmol) and imidazole (337 mg, 4.95 mmol) following the method described for Example 5. The crude product was purified by column chromatography (silica; 5% methanol in CH2Cl2) to give the title compound as a yellow solid (330 mg) m.p. 88° forms gum. δH (CDCl3) 8.43 (1H, s), 7.69 (1H, dd, J 8.2, 1.8 Hz), 7.61 (1H, dd, J 13.3, 1.8 Hz), 7.54 (2H, d, with fine splitting, J 8.6 Hz), 7.50 (1H, t, J 8.5 Hz), 7.34 (1H, s), 7.18 (1H, s), 7.04 (3H, m), 5.89 (1H, bs), 5.30-5.12 (3H, m), 4.50 (2H, dt, J 5.6, 1.4 Hz), 4.16 (2H, t, J 7.1 Hz), 3.03 (2H, t, J 7.0 Hz), 1.78 (6H, s); MS (ESI) 535 (MH+, 100%).

Workup

customThe crude product was purified by column chromatography (silica; 5% methanol in CH2Cl2)

Sources & evidence

ORD record: ord-4dd2b5455de943278cd6ee878cc2d97f
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06600037B1

Reaction notes

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