HCID 178457862, compound → HCID 178457813, compound

HRID 518698Notes

Reaction equation

HRID 518698 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[C:13]([NH:15][C@@H:16]3[CH2:21][CH2:20][C@H:19]([C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[C:12]([NH2:28])=[CH:11][N:10]=2)[CH:5]=[N:4][CH:3]=[N:2]1.[F:29][C:30]1[CH:64]=[CH:63][C:33]([C:34](/[N:36]=[C:37]2/N([C@H]3CC[C@@H](C(=O)NC(C)C)CC3)C3C=C(OCCOC)N=CC=3N/2)=[O:35])=[CH:32][CH:31]=1>>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[N:10]=[CH:11][C:12]3[NH:28]/[C:37](=[N:36]\[C:34](=[O:35])[C:33]4[CH:63]=[CH:64][C:30]([F:29])=[CH:31][CH:32]=4)/[N:15]([C@H:16]4[CH2:17][CH2:18][C@@H:19]([C:22](=[O:23])[NH:24][CH:25]([CH3:26])[CH3:27])[CH2:20][CH2:21]4)[C:13]=3[CH:14]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

3

Reactant 2

HCID 178457862HCID 178457862, compoundHCID 178496069HCID 178496069, compound

Product 1

HCID 178457813HCID 178457813, compoundYield 43%

Procedure

The title compound was prepared from cis-4-(2-(2-(1H-1,2,4-triazol-1-yl)ethoxy)-5-aminopyridin-4-ylamino)-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. Isolated as an off-white solid (62 mg, 43% yield, last step). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.08 (d, J=6.55 Hz, 6H) 1.57-1.62 (m, 2H) 1.69-1.73 (m, 2H) 2.02-2.16 (m, 2H) 2.50-2.51 (m, 1H) 2.57-2.79 (m, 2H) 3.92-4.02 (m, 1H) 4.60-4.65 (m, 4H) 4.70-4.80 (m, 1H) 6.99 (s, 1H) 7.25 (dd, J=8.85, 8.85 Hz, 2H) 7.65 (d, J=7.82 Hz, 1H) 7.98 (s, 1H) 8.22 (s, 1H) 8.28-8.36 (m, 2H) 8.53 (s, 1H) 12.70 (s, 1H). M/Z calc'd for C27H31FN8O3: 534.59. found 535 [M+H].

Workup

  1. customIsolated as an off-white solid (62 mg, 43% yield, last step)

Sources & evidence

ORD record
ord-ca56d04853244cb4b6a3db14db56aa2d
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

Loading…