Methanol → 1,1-Dimethylethyl 4-{6-methyl-5-[(1-methylethyl)oxy]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}-1-piperidinecarboxylate

HRID 2064180노트

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HRID 2064180 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[C:5]([CH3:12])=[CH:4][C:3]=1[NH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.[CH3:27][OH:28]>O1CCCC1>[CH3:12][C:5]1[C:6]([O:8][CH:9]([CH3:10])[CH3:11])=[CH:7][C:2]2[NH:1][C:27](=[O:28])[N:13]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:16][CH2:15]3)[C:3]=2[CH:4]=1

참가 물질

4

반응물 2

HCID 887MethanolHCID 598501841,1-Dimethylethyl 4-({2-amino-5-methyl-4-[(1-methylethyl)oxy]phenyl}amino)-1-piperidinecarboxylate

생성물 1

HCID 598501771,1-Dimethylethyl 4-{6-methyl-5-[(1-methylethyl)oxy]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}-1-piperidinecarboxylate수율 85%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

A solution of 1,1-dimethylethyl 4-({2-amino-5-methyl-4-[(1-methylethyl)oxy]phenyl}amino)-1-piperidinecarboxylate (D75) (0.16 mmol, 60 mg) in tetrahydrofuran (0.5 mL) was treated with N,N′-carbonyldiimidazole (0.24 mmol, 38.5 mg, 1.5 eq) under argon at room temperature, then the mixture was heated at 50° C. for 1 h, concentrated under reduced pressure, and the residue was treated with 10% aqueous sodium carbonate solution and extracted twice with ethyl acetate. The organics were combined, dried and concentrated under reduced pressure. The residue was finally purified by chromatography on silica (ethyl acetate/petrol ether then methanol) to give the title compound (0.14 mmol, 53 mg, 85% yield). M+H 390.3, 334.3, 316.3 (full molecule and fragments for loss of tert-butyl group and loss of Boc group).

후처리

  1. concentrationconcentrated under reduced pressure
  2. additionthe residue was treated with 10% aqueous sodium carbonate solution
  3. extractionextracted twice with ethyl acetate
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was finally purified by chromatography on silica (ethyl acetate/petrol ether

출처 및 근거

ORD 기록
ord-dfb0e1c9cac241f1a06079111d42083e
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288412B2

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