Ammonia → HCID 178458675, compound

HRID 518735Notes

Reaction equation

HRID 518735 reaction equation
[F:1][C:2]1[CH:39]=[CH:38][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][CH:31]([C:34]([OH:37])([CH3:36])[CH3:35])[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]([OH:22])=[O:21])[CH2:16][CH2:15]2)=[O:7])=[CH:4][CH:3]=1.[NH3:40]>O1CCOCC1>[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][CH:31]([C:34]([OH:37])([CH3:36])[CH3:35])[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:38]=[CH:39][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:15][CH2:16]1)(=[O:21])[NH2:40].[F:1][C:2]1[CH:3]=[CH:4][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[CH2:29][CH2:30][CH:31]([C:34]([OH:37])([CH3:35])[CH3:36])[CH2:32][CH2:33]4)=[CH:23][C:12]=3[N:13]\2[C@H:14]2[CH2:19][CH2:18][C@@H:17]([C:20]([N:40]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[O:22])[CH2:16][CH2:15]2)=[O:7])=[CH:38][CH:39]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 178458676HCID 178458676, compound

Product 2

HCID 178458673HCID 178458673, compoundHCID 178458675HCID 178458675, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared from cis-4-((E)-2-(4-fluorobenzoylimino)-6-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-2,3-dihydro-1H-benzo[d]imidazol-1-yl)cyclohexanecarboxylic acid and 0.5-M ammonia in dioxane using a method analogous to that used in the preparation of (E)-4-fluoro-N-(6-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-1-(cis-4-(piperazine-1-carbonyl)cyclohexyl)-1H-benzo[d]imidazol-2(3H)-ylidene)benzamide (68 mg, 68% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.03 (s, 6H), 1.20-1.35 (m, 3H), 1.55-1.78 (m, 6H), 1.78-1.90 (m, 2H), 2.16-2.24 (m, 2H), 2.55 (br. s., 1H), 2.71-2.94 (m, 4H), 3.50 (br. s., 2H), 4.01 (s, 1H), 4.76 (br. s., 1H), 6.91 (br. s., 1H), 7.16 (d, J=7.6 Hz, 1H), 7.29 (dd, J=8.9 Hz, 8.9 Hz, 2H), 7.35 (s, 1H), 7.48 (d, J=8.4 Hz, 1H), 7.55 (s, 1H), 8.29 (dd, J=8.7, 6.1 Hz, 2H), 12.73 (br. s., 1H). MS, m/z (C30H38FN5O3): calcd, 535.3. found, 536.1 [M+H].

Sources & evidence

ORD record
ord-b765d64177ef41d9afb024595a1af66a
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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