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

HRID 729753ノート

反応式

HRID 729753 の反応式
CC([O:5][C:6](=[O:46])[C@H:7]([CH2:20][NH:21][C:22]1[C:27]([CH2:28][CH3:29])=[C:26]([N:30]2[CH2:35][CH2:34][CH:33]([C:36]3[N:45]=[C:44]4[C:39]([CH2:40][CH2:41][CH2:42][NH:43]4)=[CH:38][CH:37]=3)[CH2:32][CH2:31]2)[N:25]=[CH:24][N:23]=1)[NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)(=[O:11])=[O:10])(C)C.FC(F)(F)C(O)=O.ClCCl.CO.O.C(O)(=O)C.C1(C)C=CC=CC=1>ClCCl>[CH2:28]([C:27]1[C:22]([NH:21][CH2:20][C@@H:7]([C:6]([OH:46])=[O:5])[NH:8][S:9]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)(=[O:10])=[O:11])=[N:23][CH:24]=[N:25][C:26]=1[N:30]1[CH2:35][CH2:34][CH:33]([C:36]2[N:45]=[C:44]3[C:39]([CH2:40][CH2:41][CH2:42][NH:43]3)=[CH:38][CH:37]=2)[CH2:32][CH2:31]1)[CH3:29]

参加物

6

反応物 4

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 18914200Dichloromethane methanol acetic acid waterHCID 57832825(1,1-dimethylethyl) 3-[[5-ethyl-6-[4-(1,2,3,4-tetrahydro-1,8-naphthyridin-7-yl)-1-piperidinyl]-4-pyrimidinyl]amino]-N-(4-methoxy-benzenesulphonyl)alaninate

生成物 1

HCID 578328363-[[5-ethyl-6-[4-(1,2,3,4-tetrahydro-1,8-naphthyridin-7-yl)-1-piperidinyl]-4-pyrimidinyl]amino]-N-(4-methoxy-benzenesulphonyl)alanine収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

55.8 mg (0.086 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-(4-methoxy-benzenesulphonyl)alaninate in 5 ml of dichloromethane with 0.5 ml of trifluoroacetic acid is stirred at ambient temperature until the starting product disappears according to TLC (silicagel, eluent: CH2Cl2-MeOH-H2O—AcOH 85-15-2-2). 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. 59.8 mg (Yield=85% expressed as ditrifluoroacetate) of expected product is obtained.

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-bf91861d73f246d091d0bb327a6bc12b
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…