Ammonia → HCID 178454594, compound

HRID 518730Notes

Reaction equation

HRID 518730 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.[NH3:36]>CO>[C:20]([C@@H:17]1[CH2:18][CH2:19][C@H:14]([N:13]2[C:12]3[CH:23]=[C:24]([CH2:27][N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)[CH:25]=[CH:26][C:11]=3[NH:10]/[C:9]/2=[N:8]\[C:6](=[O:7])[C:5]2[CH:34]=[CH:35][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:15][CH2:16]1)(=[O:21])[NH2:36].[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:36][C:5]([CH3:34])([CH3:4])[CH2:6][OH:7])[CH2:16][CH2:15]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 178522615HCID 178522615, compound

Product 2

HCID 178454594HCID 178454594, compoundYield 40%HCID 178513946HCID 178513946, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 1 M ammonia in MeOH 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 (19.5 mg, 40% yield). MS, m/z (C26H30FN5O3): calcd, 479.2. found, 480.2 [M+H].

Sources & evidence

ORD record
ord-c257727f844a49bea575a0135b21524e
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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