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Triethylamine → N-(3-Hydroxy-4-methyl-phenyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-benzamide

HRID 883867
ノート
印刷プレビュー

反応式

HRID 883867 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([CH3:9])=[CH:4][CH:3]=1.[CH:10]([C:13]1[CH:14]=[CH:15][C:16]2[C:21]([NH:22][C:23]3[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=3[S:32][C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)[C:26](Cl)=[O:27])=[N:20][CH:19]=[N:18][C:17]=2[N:41]=1)([CH3:12])[CH3:11].C(N(CC)CC)C>ClCCl>[OH:8][C:6]1[CH:7]=[C:2]([NH:1][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][C:31]([S:32][C:33]3[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=3)=[C:23]([NH:22][C:21]3[C:16]4[CH:15]=[CH:14][C:13]([CH:10]([CH3:11])[CH3:12])=[N:41][C:17]=4[N:18]=[CH:19][N:20]=3)[CH:24]=2)[CH:3]=[CH:4][C:5]=1[CH3:9]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 178185-Amino-2-methylphenolHCID 866155503-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-benzoyl chloride

生成物 1

HCID 67040159N-(3-Hydroxy-4-methyl-phenyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-benzamide収率 65%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

A solution of 5-amino-o-cresol (20.4 mg, 0.1655 mmol) and the product from Example 14B (70 mg, 0.1655 mmol) in dichloromethane (4 mL) was treated with triethylamine (0.025 mL, 0.1806 mmol) at room temperature. The resulting solution was stirred for 18 hours. The reaction mixture was then washed with water and brine, and the combined organic layers were dried over MgSO4, the concentrated under vacuum to give a residue which was purified by silica gel chromatography using methanol and dichloromethane as eluent to provide the title compound (55 mg, 65%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.34 (d, J=6.99 Hz, 6H), 2.07 (s, 3H), 3.17-3.28 (m, 1H), 3.77 (s, 3H), 6.86-7.10 (m, 5H), 7.30-7.46 (m, 3H), 7.64 (d, J=7.35 Hz, 1H), 7.72-7.86 (m, 1H), 7.95 (s, 1H), 8.43-8.68 (m, 1H), 8.77-8.97 (m, 1H), 9.27-9.46 (m, 1H), 10.02 (s, 1H), 10.21-10.40 (m, 1H); MS (APCI) m/z 552 (M+H)+.

後処理

  1. washThe reaction mixture was then washed with water and brine
  2. dry with materialthe combined organic layers were dried over MgSO4
  3. concentrationthe concentrated under vacuum
  4. customto give a residue which
  5. customwas purified by silica gel chromatography

出典と根拠

ORDレコード
ord-2f961c33e1ca4a37be0da1ae42fb8433
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08236950B2

反応ノート

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