1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde → N-isopropyl-2-[5-oxo-1-phenyl-4-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-phenyl-acetamide

HRID 914673

反応式

HRID 914673 の反応式
[CH:1]([N:4]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:5](=[O:28])[CH2:6][N:7]1[C:16](=[O:17])[CH2:15][C:14]2[N:10]([C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:12][N:13]=2)[C:9]2[CH:24]=[CH:25][CH:26]=[CH:27][C:8]1=2)([CH3:3])[CH3:2].[NH:35]1[C:39]2=[N:40][CH:41]=[CH:42][CH:43]=[C:38]2[C:37]([CH:44]=O)=[CH:36]1>N1C=CC=CC=1>[CH:1]([N:4]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:5](=[O:28])[CH2:6][N:7]1[C:16](=[O:17])[C:15](=[CH:44][C:37]2[C:38]3[C:39](=[N:40][CH:41]=[CH:42][CH:43]=3)[NH:35][CH:36]=2)[C:14]2[N:10]([C:11]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:12][N:13]=2)[C:9]2[CH:24]=[CH:25][CH:26]=[CH:27][C:8]1=2)([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 58957944N-isopropyl-2-(5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-phenyl-acetamide

生成物 1

HCID 136352449N-isopropyl-2-[5-oxo-1-phenyl-4-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-phenyl-acetamide収率 47.1%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

Following the procedure described for Example 1 (A), Step A, N-isopropyl-2-(5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-phenyl-acetamide (Preparation 7(A)) (500 mg, 1.10 mmol) was condensed with 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (160 mg, 1.16 mmol) in pyridine (5 mL). Purification by medium pressure chromatography eluting with a solvent gradient (5% acetone in CH2Cl2 to 50% acetone in CH2Cl2 to 10% MeOH in CH2Cl2) yielded 300 mg of N-isopropyl-2-[5-oxo-1-phenyl-4-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylene)-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-phenyl-acetamide. 1H NMR (CDCl3) δ 8.31 (d, 1H), 8.05 (d) and 7.96 (d, total 1H), 7.71 (m, 1H), 7.59 (m, 2H), 7.33-7.51 (m, 9H), 7.17 (m, 2H), 7.01 (m, 1H), 6.80 (t, 1H), 5.09 (m, 1H), 4.50 (d) and 4.30 (d, total 1H), 4.15 (m, 1H), 3.92 (d, 1H), 1.14 (m, 6H); MS 580.6 (M+1).

後処理

  1. customPurification by medium pressure chromatography
  2. washeluting with a solvent gradient (5% acetone in CH2Cl2 to 50% acetone in CH2Cl2 to 10% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-8fc3fbee48354c0a9b91c6e315533909
出典データセット
uspto-grants-2007_09
特許番号
US07265104B2

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