Quinoline → N-(4-{4-amino-7-[(1Z)-3-(diethylamino)prop-1-enyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide

HRID 1270942

反応式

HRID 1270942 の反応式
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([C:32]#[C:33][CH2:34][N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])=[CH:4][N:3]=1.N1C2C(=CC=CC=2)C=CC=1.[H][H]>C(O)C.N1C=CC=CC=1.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5](/[CH:32]=[CH:33]\[CH2:34][N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])=[CH:4][N:3]=1

参加物

6

反応物 3

HCID 7047QuinolineHCID 18451160N-(4-{4-amino-7-[3-(diethylamino)prop-1-ynyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 44432309N-(4-{4-amino-7-[(1Z)-3-(diethylamino)prop-1-enyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide収率 38%

試薬・触媒・溶媒 2

HCID 131709914Lindlars catalyst触媒HCID 21975839Pyridine ethanol溶媒

実験手順

A solution of N-(4-{4-amino-7-[3-(diethylamino)prop-1-ynyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide (0.135 g, 0.251 mmol) in ethanol/pyridine (15 mL/10 mL) was treated with Lindlar's catalyst (0.027 g), quinoline (0.05 g, 0.38 mmol), and hydrogen (55 psi) in a Parr Hydrogenator. The reaction mixture was shaken for 1H. The catalyst was filtered through celite. The solvent was removed under reduced pressure. The crude material was purified by preparative HPLC to afford 0.051 g (38%) of the title compound. 1H NMR (DMSO-d6, 400 MHz) δ 9.50 (s, 1H), 8.00–7.98 (d, 1H), 7.81 (s, 1H), 7.71–7.69 (d, 1H), 7.60–7.57 (m, 2H), 7.35–7.33 (m, 2H), 7.21–7.21 (m, 1H), 7.17–7.13 (t, H), 7.10–7.08 (d, 1H), 6.56–6.53 (d, 1H), 5.90–5.88 (dt, 1H), 5.60 (brs, 2H), 4.04 (s, 3H), 3.91 (s, 3H), 3.30–3.28 (m, 2H), 2.49–2.44 (q, 4H), 0.93–0.89 (t, 6H); LCMS (conditions a) Rt 3.28 min (95%), MH+ 540.3.

後処理

  1. filtrationThe catalyst was filtered through celite
  2. customThe solvent was removed under reduced pressure
  3. customThe crude material was purified by preparative HPLC

出典と根拠

ORDレコード
ord-9b788db0a1d64a879bf2340464709964
出典データセット
uspto-grants-2007_04
特許番号
US07202363B2

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