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Carbon Dioxide → N'-[5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl]-4-methoxy-6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)benzene-1,3-diamine

HRID 1842675
ノート
印刷プレビュー

反応式

HRID 1842675 の反応式
[OH-].[Na+].C1(S([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([C:21]3[C:26]([Cl:27])=[CH:25][N:24]=[C:23]([NH:28][C:29]4[CH:30]=[C:31]([NH2:44])[C:32]([C:37]5[CH2:38][CH2:39][N:40]([CH3:43])[CH2:41][CH:42]=5)=[CH:33][C:34]=4[O:35][CH3:36])[N:22]=3)=[CH:13]2)(=O)=O)C=CC=CC=1.C(=O)=O>CO>[Cl:27][C:26]1[C:21]([C:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:12][CH:13]=2)=[N:22][C:23]([NH:28][C:29]2[CH:30]=[C:31]([NH2:44])[C:32]([C:37]3[CH2:38][CH2:39][N:40]([CH3:43])[CH2:41][CH:42]=3)=[CH:33][C:34]=2[O:35][CH3:36])=[N:24][CH:25]=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 280Carbon DioxideHCID 14798Sodium HydroxideHCID 86677326N'-{4-[1-(benzenesulfonyl)indol-3-yl]-5-chloropyrimidin-2-yl}-4-methoxy-6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)benzene-1,3-diamine2 回

生成物 1

HCID 86677231N'-[5-chloro-4-(1H-indol-3-yl)pyrimidin-2-yl]-4-methoxy-6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)benzene-1,3-diamine収率 47.1%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

実験手順

NaOH (2M, 1.488 mL, 2.98 mmol) was added in one portion to a mixture of N′-{4-[1-(benzenesulfonyl)indol-3-yl]-5-chloropyrimidin-2-yl}-4-methoxy-6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)benzene-1,3-diamine (Intermediate 8, 283 mg, 0.47 mmol) in CH3OH (6 mL) at r.t. under N2. The resulting solution was stirred at reflux for 0.5 h. Dry ice was then added and the resulting mixture was concentrated in vacuo. The resulting residue was triturated with CH2Cl2/CH3OH (4:1, 20 mL), filtered and the filtrate was concentrated in vacuo to give a residue. Purification by FCC, eluting with 2-10% methanolic ammonia in CH2Cl2 gave the title compound (102 mg, 47%) as a pale yellow powder; 1H NMR: 2.30 (3H, s), 2.41 (2H, s), 2.60 (2H, t), 3.02 (2H, d), 3.70 (3H, s), 4.27 (2H, s), 5.73 (1H, s), 6.65 (1H, s), 7.08 (1H, t), 7.17-7.23 (1H, m), 7.26 (1H, s), 7.48 (1H, d), 8.18 (1H, s), 8.38 (1H, s), 8.41 (1H, d), 8.49 (1H, s), 11.85 (1H, s); m/z: ES+ MH+ 460.

後処理

  1. temperatureat reflux for 0.5 h
  2. concentrationthe resulting mixture was concentrated in vacuo
  3. customThe resulting residue was triturated with CH2Cl2/CH3OH (4:1, 20 mL)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto give a residue
  7. customPurification by FCC
  8. washeluting with 2-10% methanolic ammonia in CH2Cl2

出典と根拠

ORDレコード
ord-9de4368fe987421f8c4e87b502ebd42a
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

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