Ammonia → HCID 141598112, compound

HRID 343338Notes

Reaction equation

[NH2:1][C:2]([NH:4][C:5]([N:7]=[C:8]([N:16]1[CH2:21][CH2:20][CH:19]([CH2:22][C:23]([N:25]2[CH2:30][CH2:29][N:28]([CH:31]3[C:37]4=[N:38][CH:39]=[C:40]([Br:42])[CH:41]=[C:36]4[CH2:35][CH2:34][C:33]4[CH:43]=[C:44]([Cl:47])[CH:45]=[CH:46][C:32]3=4)[CH2:27][CH2:26]2)=[O:24])[CH2:18][CH2:17]1)OC1C=CC=CC=1)=[O:6])=[O:3].[NH3:48]>C1COCC1>[NH2:1][C:2]([NH:4][C:5]([NH:7][C:8]([N:16]1[CH2:17][CH2:18][CH:19]([CH2:22][C:23]([N:25]2[CH2:30][CH2:29][N:28]([CH:31]3[C:37]4=[N:38][CH:39]=[C:40]([Br:42])[CH:41]=[C:36]4[CH2:35][CH2:34][C:33]4[CH:43]=[C:44]([Cl:47])[CH:45]=[CH:46][C:32]3=4)[CH2:27][CH2:26]2)=[O:24])[CH2:20][CH2:21]1)=[NH:48])=[O:6])=[O:3]

Participants

Conditions

Temperature: 25 °C

Procedure

Phenyl N-[[(aminocarbonyl)amino]carbonyl]-4-[2-[4-(3-bromo-8-chloro-6,11-dihydro-5 H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl)-1-piperazinyl]-2-oxoethyl]-1-piperidine-carboximidate (Formula 16.1) (0.2943 g, 0.462 mmoles) was dissolved in a saturated solution of ammonia in anhydrous THF (80 ml) and the mixture was stirred at 25° C. for 19 h in a sealed vessel. The solution was evaporated to dryness and the residue was chromatographed on silica gel using 3% (10% conc. ammonium hydroxide in methanol)-dichloromethane as the eluant to give the title compound (Formula 17.1) (0.2663 g, 40%), ESIMS: m/z 645.2 (MH+).

Workup

customThe solution was evaporated to dryness
customthe residue was chromatographed on silica gel using 3% (10% conc. ammonium hydroxide in methanol)-dichloromethane as the eluant

Sources & evidence

ORD record: ord-83be910202284965bc662cbf75d615b0
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05861395

Reaction notes

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