O-Methylhydroxylamine → HCID 178454594, compound

HRID 518731Notes

Reaction equation

HRID 518731 reaction equation
[F:1][C:2]1[CH:35]=[CH:34][C:5]([C:6](/[N:8]=[C:9]2\[NH:10][C:11]3[CH:26]=[CH:25][C:24]([CH2:27][N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:23][C:12]=3[N:13]\2[C@@H:14]2[CH2:19][CH2:18][C@H:17]([C:20](Cl)=[O:21])[CH2:16][CH2:15]2)=[O:7])=[CH:4][CH:3]=1.[CH3:36][O:37][NH2:38]>>[F:1][C:2]1[CH:35]=[CH:34][C:5]([C:6](/[N:8]=[C:9]2\[NH:10][C:11]3[CH:26]=[CH:25][C:24]([CH2:27][N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:23][C:12]=3[N:13]\2[C@H:14]2[CH2:19][CH2:18][C@@H:17]([C:20](=[O:21])[NH:38][O:37][CH3:36])[CH2:16][CH2:15]2)=[O:7])=[CH:4][CH:3]=1.[F:1][C:2]1[CH:35]=[CH:34][C:5]([C:6](/[N:8]=[C:9]2\[NH:10][C:11]3[CH:26]=[CH:25][C:24]([CH2:27][N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:23][C:12]=3[N:13]\2[C@H:14]2[CH2:19][CH2:18][C@@H:17]([C:20](=[O:21])[NH:10][C:11]([CH3:26])([CH3:12])[CH2:36][OH:37])[CH2:16][CH2:15]2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4113O-MethylhydroxylamineHCID 178522615HCID 178522615, compound

Product 2

HCID 178454594HCID 178454594, compoundYield 54%HCID 178502895HCID 178502895, compound

Procedure

The title compound was prepared from cis-4-((E)-2-(4-fluorobenzoylimino)-6-(morpholinomethyl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)cyclohexanecarbonyl chloride and O-methylhydroxylamine using a method analogous to that used in the preparation of (E)-4-fluoro-N-(1-(cis-4-(1-hydroxy-2-methylpropan-2-ylcarbamoyl)cyclohexyl)-6-(morpholinomethyl)-1H-benzo[d]imidazol-2(3H)-ylidene)benzamide (27.4 mg, 54% yield). MS, m/z (C27H32FN5O4): calcd, 509.2. found, 510.2 [M+H].

Sources & evidence

ORD record
ord-5fc243f5aca3451fa26a0cafc183290d
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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