HCID 178452063, compound → HCID 178522618, compound

HRID 518624Notes

Reaction equation

HRID 518624 reaction equation
[C:1](/[N:9]=[C:10]1/[N:11]([CH:28]2[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]2)[C:12]2[CH:17]=[C:16]([O:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[N:15]=[CH:14][C:13]=2[NH:27]/1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1C=CC(C(/N=C2/N([C@H]3CC[C@@H](C(N4CCNC[C@H]4C)=O)CC3)C3C=C(OCCN4CCCCC4)N=CC=3N/2)=O)=CC=1)#N>>[N:21]1([CH2:20][CH2:19][O:18][C:16]2[N:15]=[CH:14][C:13]3[NH:27]/[C:10](=[N:9]\[C:1](=[O:8])[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)/[N:11]([CH:28]4[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]4)[C:12]=3[CH:17]=2)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

3

Reactant 2

HCID 178452063HCID 178452063, compoundHCID 178461564HCID 178461564, compound

Product 1

HCID 178522618HCID 178522618, compound

Procedure

The title compound was prepared from (E)-tert-butyl 4-(2-(benzoylimino)-6-(2-(piperidin-1-yl)ethoxy)-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)piperidine-1-carboxylate using a method analogous to the preparation of (E)-4-cyano-N-(1-(cis-4-((R)-2-methylpiperazine-1-carbonyl)cyclohexyl)-6-(2-(piperidin-1-yl)ethoxy)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)benzamide (1.9 g, 97%). MS m/z=449.2 [M+H]. Calc'd for C25H32N6O2: 448.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.16-1.29 (m, 2H) 1.31-1.42 (m, 2H) 1.41-1.55 (m, 4H) 1.60-1.77 (m, 2H) 2.26-2.37 (m, 1H) 2.37-2.45 (m, 4H) 2.58-2.70 (m, 4H) 3.04-3.17 (m, 2H) 4.29-4.39 (m, 2H) 4.72-4.89 (m, 1H) 7.04-7.06 (m, 1H) 7.47-7.51 (m, 2H) 7.51-7.54 (m, 1H) 8.19-8.20 (m, 1H) 8.21-8.22 (m, 1H) 8.22-8.24 (m, 1H).

Sources & evidence

ORD record
ord-6010b8d191f54bac8fda3eeb11f61c41
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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