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 729755ノート

反応式

HRID 729755 の反応式
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]

参加物

6

反応物 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

生成物 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)alanine収率 76%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-7d3bb720a0e34e19b9f95989b5d6be3a
出典データセット
uspto-grants-2009_09
特許番号
US07582640B2

反応ノート

読み込み中…