Water → HCID 57559122, compound

HRID 1094608Notes

Reaction equation

[CH3:1][NH:2][C:3]([CH:5]1[C:11]2[NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[CH2:9][CH2:8][N:7]([C:19](=[O:27])[C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH2:6]1)=[O:4].ClOC(C)(C)C.O>C(Cl)Cl>[CH3:1][NH:2][C:3]([C:5]1[C:11]2[NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[CH2:9][CH2:8][N:7]([C:19](=[O:27])[C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[CH:6]=1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-methyl 3-(4-fluorobenzoyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carbamide and TEA in DCM at 0° C. was added a cooled (0° C.) solution of tert-butyl hypochloride (57 mL, 0.5 mmol) in DCM. The reaction mixture was stirred for 1.5 hours at 0° C. Cold water was added to wash the solution. Organic layer was separated and the aqueous layer was extracted with DCM. The combined organic layers were washed by water and dried over MgSO4. Evaporation of solvent gave a crude product, which was purified by chromatography on silica gel eluting with MeOH-DCM to give the title compound (14 mg); 1H-NMR (CDCl3): δ 10.04 (1H, br s), 7.57 (2H, m), 7.52 (1H, d), 7.37 (1H, d), 7.24 (1H, m), 7.12 (4H, m) 5.9 (1H, br s), 4.15 (2H, t), 3.27 (2H, t), 2.92 (3H, d); MS (ES): 378 (MH+).

Workup

washto wash the solution
customOrganic layer was separated
extractionthe aqueous layer was extracted with DCM
washThe combined organic layers were washed by water
dry with materialdried over MgSO4
customEvaporation of solvent
customgave a crude product, which
customwas purified by chromatography on silica gel eluting with MeOH-DCM

Sources & evidence

ORD record: ord-77e1ffe10f2441a49ffc3c6e4b6fdf91
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133992B2

Reaction notes

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