Triethylamine → HCID 9955521、化合物

HRID 1375595ノート

反応式

HRID 1375595 の反応式
CCCP(=O)=O.[CH3:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][C:9]=1[NH:17][C:18]1[N:23]=[C:22]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH:21]=[CH:20][N:19]=1.[CH2:30]([N:32]([CH2:40][CH3:41])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([NH2:39])[CH:34]=1)[CH3:31].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:40]([N:32]([CH2:30][CH3:31])[C:33]1[CH:34]=[C:35]([NH:39][C:12](=[O:13])[C:11]2[CH:15]=[CH:16][C:8]([CH3:7])=[C:9]([NH:17][C:18]3[N:23]=[C:22]([C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[CH:21]=[CH:20][N:19]=3)[CH:10]=2)[CH:36]=[CH:37][CH:38]=1)[CH3:41]

参加物

7

反応物 5

HCID 8471TriethylamineHCID 292925N1,N1-Diethylbenzene-1,3-diamineHCID 516892Sodium BicarbonateHCID 104028804-Methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acidHCID 16167369Propylphosphoric anhydride

生成物 1

HCID 9955521HCID 9955521、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution containing ˜50% of propylphosphonic anhydride in N,N-dimethylformamide (Fluka, Buchs, Switzerland; 674 μL, ˜1.05 mmol) is added within 20 minutes to a stirred mixture of 4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-benzoic acid (214.4 mg, 0.7 mmol), N,N-diethyl-1,3-benzenediamine (115 mg, 0.7 mmol) and triethylamine (776 μL , 5.6 mmol) in 2 mL N,N-dimethylformamide. After stirring for 24 hours at room temperature, the mixture is treated with a half-saturated aqueous solution of sodium hydrogen carbonate and extracted three times with ethyl acetate. The solvent is evaporated off under reduced pressure and the residue dried in vacuo. The crude product is purified by chromatography on silica gel, eluent 2% methanol in dichloromethane and crystallised from acetone to give the title compound as a crystalline solid. 1H-NMR (400 MHz, DMSO-d6, δ): 1.07 (t, 6H); 2.31 (s, 3H); 3.29 (m, 4H); 6.38 (m, 1H); 7.06 (m, 2H); 7.11 (m, 1H); 7.36 (d, 1H); 7.43–7.50 (m, 2H); 7.67 (m, 1H); 8.21 (m, 1H); 8.43 (m, 1H); 8.51 (d, 1H); 8.66 (dd, 1H); 9.12 (s, 1H); 9.24 (m, 1H); 9.90 (s, 1H).

後処理

  1. extractionextracted three times with ethyl acetate
  2. customThe solvent is evaporated off under reduced pressure
  3. customthe residue dried in vacuo
  4. customThe crude product is purified by chromatography on silica gel, eluent 2% methanol in dichloromethane
  5. customcrystallised from acetone

出典と根拠

ORDレコード
ord-757b92e451f24f40902632e3ac0c6242
出典データセット
uspto-grants-2007_01
特許番号
US07169791B2

反応ノート

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