Indole-3-Carboxaldehyde → HCID 136347729, compound
Reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:24]3[C:18]([CH2:19][C:20](=[O:44])[N:21]([CH2:29][C:30]([N:32]([CH:41]([CH3:43])[CH3:42])[C:33]4[CH:34]=[N:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=4)=[O:31])[C:22]4[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=43)=[N:17][N:16]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:45]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:47]([CH:54]=O)=[CH:46]1>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:24]3[C:18]([C:19](=[CH:54][C:47]4[C:48]5[C:53](=[CH:52][CH:51]=[CH:50][CH:49]=5)[NH:45][CH:46]=4)[C:20](=[O:44])[N:21]([CH2:29][C:30]([N:32]([CH:41]([CH3:42])[CH3:43])[C:33]4[CH:34]=[N:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=4)=[O:31])[C:22]4[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=43)=[N:17][N:16]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Procedure
Following the procedure described for Example 1 (A), Step A, 2-[1-(3-benzyloxy-phenyl)-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-(6-methoxy-pyridin-3-yl)-acetamide (Preparation 6) (129 mg, 0.219 mmol) was condensed with 1H-indole-3-carbaldehyde (70 mg, 0.48 mmol). Purification by medium pressure chromatography eluting with a solvent gradient (10% EtOAc in hexanes to 100% EtOAc) yielded 60 mg of 2-[1-(3-benzyloxy-phenyl)-4-(1H-indol-3-ylmethylene)-5-oxo-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-(6-methoxy-pyridin-3-yl)-acetamide. 1H NMR (CD3OD) δ 8.13 (m, 1H), 7.64 (m, 2H), 7.23-7.48 (m, 13H), 7.13 (m, 3H), 6.93 (m, 2H), 4.94 (m, 2H), 4.85 (m, 1H), 4.63 (m, 1H), 4.20-4.40 (m, 1H), 3.96 (m, 1H), 3.85 (d, 1H), 0.90-1.05 (m, 6H); MS 716.5 (M+1), 714.6 (M−1)
Workup
- customPurification by medium pressure chromatography
- washeluting with a solvent gradient (10% EtOAc in hexanes to 100% EtOAc)
Sources & evidence
- ORD record
- ord-42a34a7bf485433daa82b5017fe69170
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07265104B2
Reaction notes
Loading…