4-Fluorobenzoyl isothiocyanate → HCID 178522619, compound

HRID 518664Notes

Reaction equation

HRID 518664 reaction equation
C([C:3]1[CH:43]=[CH:42][C:6]([C:7](/[N:9]=[C:10]2/[N:11]([C@H:28]3[CH2:33][CH2:32][C@@H:31]([C:34]([N:36]4[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]4)=[O:35])[CH2:30][CH2:29]3)[C:12]3[CH:17]=[C:16]([O:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)[N:15]=[CH:14][C:13]=3[NH:27]/2)=[O:8])=[CH:5][CH:4]=1)#N.[F:44]C1C=CC(C(N=C=S)=O)=CC=1>>[F:44][C:3]1[CH:43]=[CH:42][C:6]([C:7](/[N:9]=[C:10]2/[N:11]([C@H:28]3[CH2:29][CH2:30][C@@H:31]([C:34]([N:36]4[CH2:37][CH2:38][NH:39][CH2:40][CH2:41]4)=[O:35])[CH2:32][CH2:33]3)[C:12]3[CH:17]=[C:16]([O:18][CH2:19][CH2:20][N:21]4[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]4)[N:15]=[CH:14][C:13]=3[NH:27]/2)=[O:8])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 2490894-Fluorobenzoyl isothiocyanateHCID 178509875HCID 178509875, compound

Product 1

HCID 178522619HCID 178522619, compound

Procedure

The title compound was prepared using a method analagous to the preparation of (E)-4-cyano-N-(1-(cis-4-(piperazine-1-carbonyl)cyclohexyl)-6-(2-(piperidin-1-yl)ethoxy)-1H-imidazo[4,5-c]pyridin-2(3H)-ylidene)benzamide, using 4-fluorobenzoyl isothiocyanate. MS m/z=578.2 [M+H], calc 577.69 for C31H40FN7O3. 1H NMR (CDCl3) δ ppm: 8.35 (dd, J=8.7, 5.7 Hz, 2H), 8.09 (s, 1H), 7.01-7.20 (m, 3H), 4.75-4.96 (m, 1H), 4.50 (t, J=1.0 Hz, 2H), 3.64-3.77 (m, 2H), 3.46-3.59 (m, 2H), 2.80-3.03 (m, 10H), 2.53-2.69 (m, 4H), 2.08-2.19 (m, 2H), 1.72-1.90 (m, 5H), 1.60-1.71 (m, 4H), 1.40-1.55 (m, 2H).

Sources & evidence

ORD record
ord-0506c77618714bac92bfd7a6abc385cf
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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