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

HRID 729755노트

반응식

HRID 729755 반응식
CC([O:5][C:6](=[O:41])[C@H:7]([CH2:15][NH:16][C:17]1[C:22]([CH2:23][CH3:24])=[C:21]([N:25]2[CH2:30][CH2:29][CH:28]([C:31]3[N:40]=[C:39]4[C:34]([CH2:35][CH2:36][CH2:37][NH:38]4)=[CH:33][CH:32]=3)[CH2:27][CH2:26]2)[N:20]=[CH:19][N:18]=1)[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)(C)C.FC(F)(F)C(O)=O.ClCCl.CO.O.C(O)(=O)C.C1(C)C=CC=CC=1>ClCCl>[CH2:23]([C:22]1[C:17]([NH:16][CH2:15][C@@H:7]([C:6]([OH:41])=[O:5])[NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[N:18][CH:19]=[N:20][C:21]=1[N:25]1[CH2:30][CH2:29][CH:28]([C:31]2[N:40]=[C:39]3[C:34]([CH2:35][CH2:36][CH2:37][NH:38]3)=[CH:33][CH:32]=2)[CH2:27][CH2:26]1)[CH3:24]

참가 물질

6

반응물 4

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 18914200Dichloromethane methanol acetic acid waterHCID 57832859(1,1-dimethylethyl) 3-[[5-ethyl-6-[4-(1,2,3,4-tetrahydro-1,8-naphthyridin-7-yl)-1-piperidinyl]-4-pyrimidinyl]amino]-N-(2-pyridinyl)alaninate

생성물 1

HCID 578328483-[[5-ethyl-6-[4-(1,2,3,4-tetrahydro-1,8-naphthyridin-7-yl)-1-piperidinyl]-4-pyrimidinyl]amino]-N-(2-pyridinyl)alanine수율 76%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

13 mg (0.023 mmole) 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-(2-pyridinyl)alaninate in 2 ml of dichloromethane with 0.2 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 then poured into diisopropyl ether. The precipitate is filtered. 13 mg (Yield=76% expressed as ditrifluoroacetate) of expected product is obtained in the form of a beige 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-7d3bb720a0e34e19b9f95989b5d6be3a
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582640B2

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