1,2-Dichloroethane → HCID 67072439、化合物

HRID 2098461ノート

反応式

HRID 2098461 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:17][C@@H:16]2[CH2:18][C@H:13]1[CH2:14][N:15]2[C:19](=[O:26])[C@@H:20]([NH2:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[O:11].[CH3:27][C:28]1[CH:36]=[C:35]2[C:31]([CH:32]=[C:33]([C:37](O)=[O:38])[NH:34]2)=[CH:30][CH:29]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl.O>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:17][C@@H:16]2[CH2:18][C@H:13]1[CH2:14][N:15]2[C:19]([C@@H:20]([NH:25][C:37]([C:33]1[NH:34][C:35]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[C:28]([CH3:27])[CH:36]=2)=[O:38])[C:21]([CH3:22])([CH3:23])[CH3:24])=[O:26])=[O:11]

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 31633966-Methyl-1H-indole-2-carboxylic acidHCID 58286598HCID 58286598、化合物

生成物 1

HCID 67072439HCID 67072439、化合物収率 60.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of (2S)-1-[(1S,4S)-5-(1H-benzimidazol-2-ylcarbonyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]-3,3-dimethyl-1-oxo-2-butanamine (120 mg, 0.34 mmol), 6-methyl-1H-indole-2-carboxylic acid (60 mg, 0.34 mmol), EDC (78 mg, 0.41 mmol), HOBt (9 mg, 0.068 mmol), NMM (103 mg, 1.02 mmol) in CH2Cl2 (2 mL) was stirred at room temperature for 18 h. The reaction was diluted with water and CH2Cl2 then washed with sat. NaHCO3 (20 mL) and brine (20 mL). The solution was dried over anhydrous Na2SO4 and concentrated to give the crude product, which was purified by reverse phase HPLC: 50-80% ACN/Water (0.1% TFA). Concentration of the fractions containing product afforded the title compound (105 mg) as a white solid. LCMS (m/z): 513.1 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm: 0.90-1.10 (m, 9H), 1.75-2.20 (m, 2H), 2.30-2.40 (m, 3H), 3.45-3.95 (m, 3H), 4.00-5.25 m, 4H), 6.20-6.75 (m, 1H), 6.80-7.70 (m, 9H), 9.30-9.70 (m, 1H)

後処理

  1. washthen washed with sat. NaHCO3 (20 mL) and brine (20 mL)
  2. dry with materialThe solution was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customto give the crude product, which
  5. customwas purified by reverse phase HPLC
  6. additionConcentration of the fractions containing product

出典と根拠

ORDレコード
ord-902f6497c96a446c9569eb7924b69e51
出典データセット
uspto-grants-2013_05
特許番号
US08450484B2

反応ノート

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