4-Methylmorpholine → HCID 136380434, 화합물

HRID 1354637

반응식

HRID 1354637 반응식
Cl[C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]#[N:19])[CH:15]=[C:14]([CH3:20])[C:12]=2[N:13]=1.CN1CCOCC1.[NH2:28][C@@H:29]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:30][OH:31]>CN(C=O)C>[OH:31][CH2:30][C@@H:29]([NH:28][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]#[N:19])[CH:15]=[C:14]([CH3:20])[C:12]=2[N:13]=1)[CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

참가 물질

5

반응물 3

HCID 79724-MethylmorpholineHCID 447213phenylalaninol, (S)-HCID 1356816422-(4-Chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-7-methyl-3H-benzimidazole-5-carbonitrile

생성물 1

HCID 136380434HCID 136380434, 화합물수율 68%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

To a solution of 2-(4-chloro-2-oxo-1,2-dihydro-pyridin-3-yl)-7-methyl-3H-benzimidazole-5-carbonitrile (0.7 g, 2.19 mmol) in DMF (15 mL) were added N-methylmorpholine (0.66 g, 6.57 mmol) and (S)-(−)-2-amino-3-phenyl-1-propanol (0.40 g, 2.63 mmol). The reaction mixture was heated to 80° C. for 6 h and then cooled to room temperature. After concentration in vacuo, the residue was purified by flash chromatography (3% MeOH/CH2Cl2) to yield the title compound (0.59 g, 68%) as a yellow foam. 1H NMR (400 MHz, CD3OD) δ 7.74 (1H, s), 7.63 (1H, s), 7.12–7.27 (6H, m), 6.07 (1H, d, J=7.5 Hz), 3.97 (1H, m), 3.74 (2H, t, J=5 Hz), 3.14 (1H, dd, J=5.5, 14.0 Hz), 2.94 (1H, dd, J=7.9, 14.0 Hz), 2.60 (3H, s). LCMS (M+H)+ m/z 400 (t=1.71 min.).

후처리

  1. temperaturecooled to room temperature
  2. concentrationAfter concentration in vacuo
  3. customthe residue was purified by flash chromatography (3% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-d718435acd144e0d890eea0921d7d3a1
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223757B2

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