HCID 178457860, compound → HCID 178457806, compound

HRID 518702Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([O:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:4][C:3]=1[NH:18][C@@H:19]1[CH2:24][CH2:23][C@H:22]([C:25]([NH:27][CH:28]([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1.[F:31][C:32]1[CH:66]=[CH:65][C:35]([C:36](/[N:38]=[C:39]2/N([C@H]3CC[C@@H](C(=O)NC(C)C)CC3)C3C=C(OCCOC)N=CC=3N/2)=[O:37])=[CH:34][CH:33]=1>>[F:31][C:32]1[CH:33]=[CH:34][C:35]([C:36](/[N:38]=[C:39]2\[NH:1][C:2]3[CH:7]=[C:6]([F:8])[C:5]([O:9][CH2:10][CH2:11][N:12]4[CH2:13][CH2:14][O:15][CH2:16][CH2:17]4)=[CH:4][C:3]=3[N:18]\2[C@H:19]2[CH2:24][CH2:23][C@@H:22]([C:25](=[O:26])[NH:27][CH:28]([CH3:30])[CH3:29])[CH2:21][CH2:20]2)=[O:37])=[CH:65][CH:66]=1

Participants

Reactant 2

HCID 178457860HCID 178457860, compound

HCID 178496069HCID 178496069, compound

Product 1

HCID 178457806HCID 178457806, compound

Procedure

The title compound was prepared from cis-4-(2-amino-4-fluoro-5-(2-morpholinoethoxy)phenylamino)-N-isopropylcyclohexanecarboxamide using a procedure analogous to that used to prepare (E)-4-fluoro-N-(1-(cis-4-(isopropylcarbamoyl)cyclohexyl)-6-(2-methoxyethoxy)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)benzamide. The product was isolated as an off-white solid (161 mg, 81% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.08 (d, J=8 Hz, 6H) 1.53-1.66 (m, 2H) 1.70-1.80 (m, 2H) 2.00-2.08 (m, 2H) 2.52-2.60 (m, 1H) 2.70-2.91 (m, 8H) 3.49-3.70 (m, 4H) 3.89-4.08 (m, 1H) 4.27 (t, J=6.06 Hz, 2H) 4.93 (br. s., 1H) 7.24 (dd, J=8.85, 8.85 Hz, 2H) 7.38 (d, J=10.76 Hz, 1H) 7.77 (d, J=7.73 Hz, 2H) 8.29 (dd, J=8.61, 5.97 Hz, 2H) 12.73 (s, 1H). M/Z calc'd for C30H37F2N5O4: 569.64. found 570 [M+H].

Sources & evidence

ORD record: ord-10ea8cfef4e94a31aaf71813f8ecdf1e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115127B2

Reaction notes

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