(+/-)-2-{4-[3-(Benzhydrylidene-amino)-4-cyano-benzyl]-3-methoxycarbonyl-5-oxo-piperazin-1-ylmethyl}-5-chloro-indole-1-carboxylic acid tert-butyl ester → (+/-)-2-[4-(3-Amino-4-cyano-benzyl)-3-methoxycarbonyl-5-oxo-piperazin-1-ylmethyl]-5-chloro-indole-1-carboxylic acid tert-butyl ester

HRID 1433011노트

반응식

HRID 1433011 반응식
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH2:18][N:19]1[CH2:24][C:23](=[O:25])[N:22]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[C:29]([N:35]=C(C3C=CC=CC=3)C3C=CC=CC=3)[CH:28]=2)[CH:21]([C:49]([O:51][CH3:52])=[O:50])[CH2:20]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>Cl.CO>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH2:18][N:19]1[CH2:24][C:23](=[O:25])[N:22]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[C:29]([NH2:35])[CH:28]=2)[CH:21]([C:49]([O:51][CH3:52])=[O:50])[CH2:20]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 1

HCID 86760983(+/-)-2-{4-[3-(Benzhydrylidene-amino)-4-cyano-benzyl]-3-methoxycarbonyl-5-oxo-piperazin-1-ylmethyl}-5-chloro-indole-1-carboxylic acid tert-butyl ester

생성물 1

HCID 54288444(+/-)-2-[4-(3-Amino-4-cyano-benzyl)-3-methoxycarbonyl-5-oxo-piperazin-1-ylmethyl]-5-chloro-indole-1-carboxylic acid tert-butyl ester수율 95.3%

시약·촉매·용매 2

HCID 313Hydrochloric Acid촉매HCID 887Methanol용매

실험 절차

Partially-purified (±)-2-{4-[3-(benzhydrylidene-amino)-4-cyano-benzyl]-3-methoxycarbonyl-5-oxo-piperazin-1-ylmethyl}-5-chloro-indole-1-carboxylic acid tert-butyl ester (550 mg, 0.76 mmol) is suspended in reagent grade MeOH (20 mL). To the heterogeneous mixture is added 12M HCl (5 drops) and the reaction mixture is maintained at ambient temperature until homogeneous (˜30 min). The reaction mixture is partitioned between diethyl ether and water containing excess NaHCO3 (500 mL). The layers are separated and the organic phase is washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude residue is chromatographed on silica gel (CH2Cl2 to 2% MeOH/CH2Cl2) to provide 400 mg (94%) of the title compound which is used directly in the next reaction. MS (ISP loop): 532 (M+H).

후처리

  1. customThe reaction mixture is partitioned between diethyl ether and water containing excess NaHCO3 (500 mL)
  2. customThe layers are separated
  3. washthe organic phase is washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue is chromatographed on silica gel (CH2Cl2 to 2% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-ac3346133ff04282913c14d6a79d9305
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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