Trifluoroacetic acid → Methyl 6-{[{2-[[3-(aminosulfonyl)propyl]-(methyl)amino]ethyl}(methyl)amino]methyl}-13-cyclohexyl-5-methyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-10-carboxylate

HRID 421963ノート

反応式

HRID 421963 の反応式
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:47]([O:49][CH3:50])=[O:48])=[CH:12][C:13]=3[N:14]3[C:20]=2[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[N:17]([CH3:25])[CH:16]([CH2:26][N:27]([CH3:46])[CH2:28][CH2:29][N:30]([CH3:45])[CH2:31][CH2:32][CH2:33][S:34](=[O:44])(=[O:43])[NH:35]C(=O)OC(C)(C)C)[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:35][S:34]([CH2:33][CH2:32][CH2:31][N:30]([CH3:45])[CH2:29][CH2:28][N:27]([CH2:26][CH:16]1[CH2:15][N:14]2[C:13]3[CH:12]=[C:11]([C:47]([O:49][CH3:50])=[O:48])[CH:10]=[CH:9][C:8]=3[C:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[C:20]2[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[N:17]1[CH3:25])[CH3:46])(=[O:43])=[O:44]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 66674446methyl 13-cyclohexyl-5-methyl-6-(2,5,13,13-tetramethyl-9,9-dioxido-11-oxo-12-oxa-9-thia-2,5,10-triazatetradec-1-yl)-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-10-carboxylate

生成物 1

HCID 66675171Methyl 6-{[{2-[[3-(aminosulfonyl)propyl]-(methyl)amino]ethyl}(methyl)amino]methyl}-13-cyclohexyl-5-methyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-10-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Methyl 13-cyclohexyl-5-methyl-6-(2,5,13,13-tetramethyl-9,9-dioxido-11-oxo-12-oxa-9-thia-2,5,10-triazatetradec-1-yl)-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-10-carboxylate was dissolved in DCM (0.05M) and TFA was added. The mixture was left standing at RT. After 1 h all volatiles were evaporated in vacuo. The residual material was coevaporated with toluene. Methyl 6-{[{2-[[3-(aminosulfonyl)propyl]-(methyl)amino]ethyl}(methyl)amino]methyl}-13-cyclohexyl-5-methyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-10-carboxylate was obtained as a reddish sticky solid. The material was dissolved in MeOH/THF (0.05 M) and 1M aqueous KOH solution (4 eq.) was added. The mixture was stirred at RT overnight and then warmed for 5 h to 70° C. After cooling to RT the solution was diluted with water and adjusted with 1M aqueous HCl to pH 6. The resulting suspension was extracted with EtOAc. The combined organic phases were washed with brine and dried over Na2SO4. All volatiles were evaporated in vacuo. The residual material was used without further purification in the next reaction (95%). (ES+) m/z 611 (M+H)+.

後処理

  1. waitThe mixture was left
  2. customstanding at RT
  3. customAfter 1 h all volatiles were evaporated in vacuo

出典と根拠

ORDレコード
ord-d367f07bb31344089948327bd58fb9a3
出典データセット
uspto-grants-2012_01
特許番号
US08101595B2

反応ノート

読み込み中…