1,2-Dichloroethane → (s)-7-Chloro-2-neopentyl-4-(2-oxo-2-(4-(5-oxo-4,5-dihydro-1h-pyrrolo[3,2-b]pyridin-6-yl)piperidin-1-yl)ethyl)-1,2,4,5-tetrahydroazepino[3,4-e]indol-3(8h)-one

HRID 2378995ノート

反応式

HRID 2378995 の反応式
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[C:12](=[O:13])[NH:11][C:10]3[CH:14]=[CH:15][NH:16][C:9]=3[CH:8]=2)[CH2:3][CH2:2]1.[Cl:17][C:18]1[CH:19]=[C:20]2[CH2:31][C@@H:30]([CH2:32][C:33](O)=[O:34])[C:29](=[O:36])[N:28]([CH2:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:27][C:21]2=[C:22]2[C:26]=1[NH:25][CH:24]=[CH:23]2.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[Cl:17][C:18]1[CH:19]=[C:20]2[CH2:31][C@@H:30]([CH2:32][C:33](=[O:34])[N:1]3[CH2:2][CH2:3][CH:4]([C:7]4[C:12](=[O:13])[NH:11][C:10]5[CH:14]=[CH:15][NH:16][C:9]=5[CH:8]=4)[CH2:5][CH2:6]3)[C:29](=[O:36])[N:28]([CH2:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:27][C:21]2=[C:22]2[C:26]=1[NH:25][CH:24]=[CH:23]2

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 590063956-(piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridin-5(4H)-oneHCID 68892930(S)-2-(7-chloro-2-neopentyl-3-oxo-1,2,3,4,5,8-hexahydroazepino[3,4-e]indol-4-yl)acetic acid

生成物 1

HCID 23658028(s)-7-Chloro-2-neopentyl-4-(2-oxo-2-(4-(5-oxo-4,5-dihydro-1h-pyrrolo[3,2-b]pyridin-6-yl)piperidin-1-yl)ethyl)-1,2,4,5-tetrahydroazepino[3,4-e]indol-3(8h)-one収率 16.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To 6-(piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridin-5(4H)-one (60.0 mg, 0.276 mmol) was added (S)-2-(7-chloro-2-neopentyl-3-oxo-1,2,3,4,5,8-hexahydroazepino[3,4-e]indol-4-yl) acetic acid (100 mg, 0.276 mmol), EDC (58.3 mg, 0.304 mmol), HOBT (41.0 mg, 0.304 mmol), DMF (2.0 ml) at rt, followed by diisopropylethylamine (0.192 ml, 1.10 mmol). The resulting mixture was stirred at rt over night, partial of the solvent was removed under N2, and the residue was purified on reverse phase PrepHPLC to afford the expected products(25.2 mg, 16%), (S)-7-chloro-2-neopentyl-4-(2-oxo-2-(4-(5-oxo-4,5-dihydro-1H-pyrrolo [3,2-b]pyridin-6-yl)piperidin-1-yl)ethyl)-1,2,4,5-tetrahydroazepino [3,4-e]indol-3 (8H)-one, as a tan solid. 1H-NMR (400 MHz, MeOD) d 0.79 (d, J=5.29 Hz, 11H) 1.52-1.62 (m, 1H) 1.81 (s, 1H) 2.38-2.49 (m, 1H) 2.75 (s, 1H) 3.01 (d, J=13.35 Hz, 1H) 3.09-3.21 (m, 4H) 3.66 (d, J=13.85 Hz, 1H) 3.96 (s, 3H) 3.99-4.06 (m, 1H) 4.24 (s, 1H) 4.65 (d, J=17.37 Hz, 2H) 5.46-5.55 (m, 1H) 6.27 (dd, J=5.29, 3.02 Hz, 1H) 7.22 (s, 1H) 7.36 (dd, J=7.81, 3.02 Hz, 1H) 8.24 (s, 1H); Mass spec 562.48 (MH+) calc for C31H36ClN5O3 561.25.

後処理

  1. customwas removed under N2
  2. customthe residue was purified on reverse phase PrepHPLC

出典と根拠

ORDレコード
ord-374b439b8d5b4a9cbdb4b0614785c14d
出典データセット
uspto-grants-2008_12
特許番号
US07470680B2

反応ノート

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