Toluene → 3-[[5-ethyl-6-[4-(1,2,3,4-tetrahydro-1,8-naphthyridin-7-yl)-1-piperidinyl]-4-pyrimidinyl]amino]-N-(1-naphthalenesulphonyl)alanine

HRID 729754노트

반응식

HRID 729754 반응식
[CH2:1]([C:3]1[C:4]([NH:25][CH2:26][C@@H:27]([C:42]([O:44]C(C)(C)C)=[O:43])[NH:28][S:29]([C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[N:5][CH:6]=[N:7][C:8]=1[N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[N:24]=[C:23]3[C:18]([CH2:19][CH2:20][CH2:21][NH:22]3)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)[CH3:2].FC(F)(F)C(O)=O.ClCCl.CO.O.C(O)(=O)C.C1(C)C=CC=CC=1>ClCCl>[CH2:1]([C:3]1[C:4]([NH:25][CH2:26][C@@H:27]([C:42]([OH:44])=[O:43])[NH:28][S:29]([C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=[CH:34][CH:33]=2)(=[O:30])=[O:31])=[N:5][CH:6]=[N:7][C:8]=1[N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[N:24]=[C:23]3[C:18]([CH2:19][CH2:20][CH2:21][NH:22]3)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)[CH3:2]

참가 물질

6

반응물 4

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 18914200Dichloromethane methanol acetic acid waterHCID 57832879(1,1-dimethylethyl) 3-[[5-ethyl-6-[4-(1,2,3,4-tetrahydro-1,8-naphthyridin-7-yl)-1-piperidinyl]-4-pyrimidinyl]amino]-N-(1-naphthalenesulphonyl)alaninate

생성물 1

HCID 578329153-[[5-ethyl-6-[4-(1,2,3,4-tetrahydro-1,8-naphthyridin-7-yl)-1-piperidinyl]-4-pyrimidinyl]amino]-N-(1-naphthalenesulphonyl)alanine수율 82%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

220 mg (0.33 mmoles) of (1,1-dimethylethyl) 3-[[5-ethyl-6-[4-(1,2,3,4-tetrahydro-1,8-naphthyridin-7-yl)-1-piperidinyl]-4-pyrimidinyl]amino]-N-(1-naphthalenesulphonyl)alaninate in 20 ml of dichloromethane with 2 ml of trifluoroacetic acid is stirred at ambient temperature until the starting product disappears according to TLC (silicagel, eluent: CH2Cl2-MeOH—H2O—AcOH 90-10-1-1). Toluene is added and the reaction mixture is evaporated to dryness under reduced pressure (2 kPa). The residue is solubilized in the minimum amount of dichloromethane with a little methanol then poured into diisopropyl ether. The precipitate is filtered. 230 mg (Yield=82% expressed as ditrifluoroacetate) of expected product is obtained in the form of a white solid.

후처리

  1. customthe reaction mixture is evaporated to dryness under reduced pressure (2 kPa)
  2. additionthen poured into diisopropyl ether
  3. filtrationThe precipitate is filtered

출처 및 근거

ORD 기록
ord-a68e98e10fa144c0874b9adece06b7f3
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582640B2

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