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p-Toluenesulfonic acid monohydrate → HCID 71240803、化合物

HRID 1842670
ノート
印刷プレビュー

反応式

HRID 1842670 の反応式
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[C:5]([CH3:17])=[CH:4][N:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:30][O:31][C:32]1[CH:38]=[C:37]([C:39]2[CH2:40][CH2:41][N:42]([CH3:45])[CH2:43][CH:44]=2)[C:36]([N+:46]([O-:48])=[O:47])=[CH:35][C:33]=1[NH2:34]>CC(O)CCC>[CH3:30][O:31][C:32]1[CH:38]=[C:37]([C:39]2[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH:40]=2)[C:36]([N+:46]([O-:48])=[O:47])=[CH:35][C:33]=1[NH:34][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[C:5]([CH3:17])=[CH:4][N:3]=1
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 521998p-Toluenesulfonic acid monohydrateHCID 59291169HCID 59291169、化合物2 回HCID 866773252-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitroaniline2 回

生成物 1

HCID 71240803HCID 71240803、化合物収率 63.2%

試薬・触媒・溶媒 1

HCID 223862-Pentanol溶媒

実験手順

A solution of 3-(2-chloro-5-methylpyrimidin-4-yl)pyrazolo[1,5-a]pyridine (Intermediate 5, 271 mg, 1.00 mmol), p-toluene sulphonic acid monohydrate (271 mg, 1.43 mmol) and 2-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitroaniline (Intermediate 3, 250 mg, 0.95 mmol) were heated in 2-pentanol (12 mL) at reflux under N2 for 30 h. The mixture was then concentrated in vacuo and the residue was dissolved in CH3OH. Purification by ion exchange chromatography (SCX column), eluting with 7M methanolic ammonia, gave the title compound (283 mg, 63%) as an orange powder after trituration with CH3CN. 1H NMR: 2.28-2.36 (5H, m), 2.44 (3H, s), 2.60 (2H, t), 3.00 (2H, d), 4.00 (3H, d), 5.64 (1H, s), 6.97 (1H, s), 7.13 (1H, m), 7.40 (1H, m), 8.27 (1H, s), 8.39 (1H, s), 8.53 (1H, d), 8.61 (1H, s), 8.83 (1H, d), 8.87 (1H, s); m/z: ES− MH− 470.

後処理

  1. temperatureat reflux under N2 for 30 h
  2. concentrationThe mixture was then concentrated in vacuo
  3. dissolutionthe residue was dissolved in CH3OH
  4. customPurification by ion exchange chromatography (SCX column)
  5. washeluting with 7M methanolic ammonia

出典と根拠

ORDレコード
ord-83286be2b328412288c55d6738a26a38
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08946235B2

反応ノート

読み込み中…

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