Ethyl isocyanate → HCID 178465273, compound
Reaction equation
[Cl:1][C:2]1[C:3]([NH:22][C@@H:23]2[C@@H:28]3[CH2:29][C@@H:25]([CH:26]=[CH:27]3)[C@@H:24]2[C:30]([NH2:32])=[O:31])=[C:4]2[N:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH:16]4[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]4)[CH:15]=3)[NH:8][C:5]2=[N:6][CH:7]=1.[CH2:33]([N:35]=[C:36]=[O:37])[CH3:34]>>[CH2:33]([NH:35][C:36]([N:19]1[CH2:20][CH2:21][CH:16]([N:14]2[CH:15]=[C:11]([C:9]3[NH:8][C:5]4=[N:6][CH:7]=[C:2]([Cl:1])[C:3]([NH:22][C@H:23]5[C@@H:24]([C:30](=[O:31])[NH2:32])[C@H:25]6[CH2:29][C@@H:28]5[CH:27]=[CH:26]6)=[C:4]4[N:10]=3)[CH:12]=[N:13]2)[CH2:17][CH2:18]1)=[O:37])[CH3:34]Participants
3
Procedure
In a similar fashion as for the synthesis of Compound LXI, (1S,2S,3R,4R)-3-[6-Chloro-2-(1-piperidin-4-yl-1H-pyrazol-4-yl)-3H-imidazo[4,5-b]pyridine-7-ylamino]-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide was reacted with ethyl isocyanate to afford the title compound as a white lyophilate (70%). 1H NMR (d-chloroform): 8.36 (d, J=8 Hz, 1H), 8.11 (s, 2H), 7.87 (s, 1H), 6.47 (m, 1H), 6.42 (m, 1H), 5.81 (br s, 1H), 5.45 (br s, 1H), 5.36 (m, 1H), 4.42 (m, 2H), 4.15 (m, 2H), 3.33 (m, 2H), 3.17 (s, 1H), 3.02 (m, 3H), 2.67 (d, J=9 Hz, 1H), 2.33 (d, J=9 Hz, 1H), 2.23 (m, 2H), 2.10 (m, 3H), 1.69 (d, J=8 Hz, 1H), 1.20 (t, J=9 Hz, 1H). MS: 524.21 (M+H). HPLC retention time: 1.96 minutes (G Method).
Sources & evidence
- ORD record
- ord-56cece6b78304d30a7b6c6b640dd2766
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238656B2
Reaction notes
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