Bis-(1H-imidazol-2-YL)-methanone → 1,1-Dimethylethyl 4-(4-fluoro-6-methoxy-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinecarboxylate

HRID 2061478Notes

Reaction equation

[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([O:9][CH3:10])=[CH:4][C:3]=1[NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.[C:25](C1NC=CN=1)(C1NC=CN=1)=[O:26]>O1CCCC1>[F:8][C:7]1[C:2]2[NH:1][C:25](=[O:26])[N:11]([CH:12]3[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]3)[C:3]=2[CH:4]=[C:5]([O:9][CH3:10])[CH:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 1,1-dimethylethyl 4-[(2-amino-3-fluoro-5-methoxyphenyl)amino]-1-piperidinecarboxylate (D13a) (230 mg, 0.7 mmol), carbonyl diimidazole (150 mg, 1.0 mmol), and tetrahydrofuran (6 ml) was heated 1 h at 50° C. then partitioned between dichloromethane and water. The organic layer was purified by chromatography on silicagel eluting with 0 to 10% methanol in dichloromethane containing 0.2M ammonia to give the title compound as white crystals, 47%, 120 mg, M−−H=364.

Workup

customthen partitioned between dichloromethane and water
customThe organic layer was purified by chromatography on silicagel
washeluting with 0 to 10% methanol in dichloromethane containing 0.2M ammonia

Sources & evidence

ORD record: ord-fa6ea8481352423ba6dd04a702cfaede
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283364B2

Reaction notes

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