1-(4-Amino-quinazolin-7-ylmethyl)-4-benzyloxycarbonyl-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one → 1-(4-Amino-quinazolin-7-ylmethyl)-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one

HRID 1433060노트

반응식

HRID 1433060 반응식
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH2:17][N:16](C(OCC4C=CC=CC=4)=O)[C@@H:15]([CH2:29][CH2:30][S:31][CH3:32])[C:14]3=[O:33])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1>Br.C(O)(=O)C.CCOCC>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][CH2:17][NH:16][C@@H:15]([CH2:29][CH2:30][S:31][CH3:32])[C:14]3=[O:33])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1

참가 물질

5

반응물 1

HCID 690288501-(4-Amino-quinazolin-7-ylmethyl)-4-benzyloxycarbonyl-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one

생성물 1

HCID 670141251-(4-Amino-quinazolin-7-ylmethyl)-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one수율 42%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 260Hydrogen Bromide용매HCID 3283Diethyl Ether용매

실험 절차

1-(4-Amino-quinazolin-7-ylmethyl)-4-benzyloxycarbonyl-3-(S)-(2-methylsulfanyl-ethyl)-piperazin-2-one (100 mg, 0.215 mmol) is dissolved in 5 ml of 30% hydrogen bromide in acetic acid. The mixture is stirred for 1 hour, diluted with ethyle ether. The ether is decanted and the resulting solid is washed thoroughly with ethyle ether. The resulting crude product is purified by column chromatography eluting with a 4/2/1 mixture of CH2Cl2/MeOH/NH4OH (30% in H2O). with a gradient of 5% MeOH:CH2Cl2 to 10% MeOH:CH2Cl2. The resulting product is purified by another column chromatography eluting with a gradient of 20% MeOH:CH2Cl2 to 50% MeOH:CH2Cl2. The title bound (30 mg, 42% yield) is obtained as an off-white solid.

후처리

  1. customThe ether is decanted
  2. washthe resulting solid is washed thoroughly with ethyle ether
  3. customThe resulting crude product is purified by column chromatography
  4. washeluting with a 4/2/1 mixture of CH2Cl2/MeOH/NH4OH (30% in H2O)
  5. customThe resulting product is purified by another column chromatography
  6. washeluting with a gradient of 20% MeOH
  7. customis obtained as an off-white solid

출처 및 근거

ORD 기록
ord-dd90b56c3fbe4e41b3c761cc6d155dbc
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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