1,2-Dichloroethane → HCID 67072439, 화합물

HRID 2098461노트

반응식

HRID 2098461 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

HCID 67072439HCID 67072439, 화합물수율 60.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-902f6497c96a446c9569eb7924b69e51
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450484B2

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