HCID 178457850, compound → HCID 178457808, compound

HRID 518707Notes

Reaction equation

HRID 518707 reaction equation
[NH2:1][C:2]1[C:3]([NH:16][C@@H:17]2[CH2:22][CH2:21][C@H:20]([C:23]([NH:25][CH:26]([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)=[CH:4][C:5]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)=[N:6][CH:7]=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>>[F:29][C:30]1[CH:31]=[CH:32][C:33]([C:34](/[N:36]=[C:37]2/[N:16]([C@H:17]3[CH2:22][CH2:21][C@@H:20]([C:23](=[O:24])[NH:25][CH:26]([CH3:28])[CH3:27])[CH2:19][CH2:18]3)[C:3]3[CH:4]=[C:5]([O:8][CH:9]4[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]4)[N:6]=[CH:7][C:2]=3[NH:1]/2)=[O:35])=[CH:63][CH:64]=1

Participants

3

Reactant 2

HCID 178457850HCID 178457850, compoundHCID 178496069HCID 178496069, compound

Product 1

HCID 178457808HCID 178457808, compound

Procedure

The title compound was prepared from cis-4-(5-amino-2-(1-methylpiperidin-4-yloxy)pyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide using a procedure analogous to that used for (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 (94 mg, 72% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.10 (d, J=8H, 6H) 1.48-1.78 (m, 7H) 1.84-2.03 (m, 2H) 2.04-2.10 (m, 2H) 2.13-2.34 (m, 5H) 2.65 (m, 4H) 3.95-4.05 (m, 1H) 4.65-4.80 (m, 1H) 4.89-5.03 (m, 1H) 6.96 (s, 1H) 7.26 (dd, J=8.75 Hz, 2H) 7.68 (d, J=7.63 Hz, 1H) 8.23 (s, 1H) 8.31 (dd, J=8.56, 5.82 Hz, 2H) 12.60 (br. s., 1H). M/Z calc'd for C29H37FN6O3: 536.64. found 537 [M+H].

Sources & evidence

ORD record
ord-b765688b2aaf4b8daf5ee96f484df421
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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