4-(3-Chloropropyl)morpholine → 3-Benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1-(3-morpholinopropyl)-1H-imidazol-2-yl)isophthalate
Reaction equation
[CH2:1]([N:5]([CH2:33][CH2:34][CH2:35][CH3:36])[C:6]([C:8]1[N:9]=[C:10]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=2[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[NH:11][CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4].Cl[CH2:38][CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1>>[CH2:33]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([C:8]1[N:9]=[C:10]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=2[C:23]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24])[N:11]([CH2:38][CH2:39][CH2:40][N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)[CH:12]=1)=[O:7])[CH2:34][CH2:35][CH3:36]Participants
3
Procedure
Following a procedure analogous to that for the synthesis of Intermediate 274A, 3-benzyl 1-methyl 4-(4-(dibutylcarbamoyl)-1H-imidazol-2-yl)isophthalate (130 mg, 0.26 mmol) and 4-(3-chloropropyl)morpholine (53 mg, 0.27 mmol) were converted to the title compound. (65 mg, 40%). 1H NMR (CD3OD) δ 8.67 (d, J=2.0 Hz, 1H), 8.33 (dd, J=8.0, 1.6 Hz, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.62 (s, 1H), 7.38-7.32 (m, 5H), 5.21 (s, 2H), 4.01 (s, 3H), 3.84-3.80 (m, 4H), 3.59-3.50 (m, 6H), 2.20-2.11 (m, 6H), 1.70-1.60 (m, 6H), 1.45-1.25 (m, 4H), 1.05-0.82 (m, 6H); MS(ESI+) m/z 619 (M+H)+.
Sources & evidence
- ORD record
- ord-083b2f9d85f3460ba60638a54c94577c
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346795B2
Reaction notes
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