Acetic Acid → Methyl 13-cyclohexyl-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[2,1-a][2]benzazepine-10-carboxylate

HRID 421967ノート

反応式

HRID 421967 の反応式
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:27]([O:29][CH3:30])=[O:28])=[CH:12][C:13]=3[N:14]3[CH2:20][CH:19](C=O)[CH2:18][C:17]4[CH:23]=[CH:24][CH:25]=[CH:26][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:31]C(O)=O.[C:35]([O:39][C:40](=[O:54])[NH:41][S:42]([CH2:45][CH2:46][CH2:47][N:48]([CH3:53])[CH2:49][CH2:50][NH:51][CH3:52])(=[O:44])=[O:43])([CH3:38])([CH3:37])[CH3:36].CCN(CC)CC.[BH3-]C#N.[Na+]>CO>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:27]([O:29][CH3:30])=[O:28])=[CH:12][C:13]=3[N:14]3[CH2:20][CH:19]([CH2:52][N:51]([CH3:31])[CH2:50][CH2:49][N:48]([CH3:53])[CH2:47][CH2:46][CH2:45][S:42](=[O:43])(=[O:44])[NH:41][C:40](=[O:54])[O:39][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:18][C:17]4[CH:23]=[CH:24][CH:25]=[CH:26][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

7

反応物 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 86640308Tert-butyl[(3-{methyl[2-(methylamino)ethyl]amino}propyl)sulfonyl]carbamateHCID 86640311Methyl 13-cyclohexyl-6-formyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

生成物 1

HCID 66674850Methyl 13-cyclohexyl-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[2,1-a][2]benzazepine-10-carboxylate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Methyl 13-cyclohexyl-6-formyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate was dissolved in MeOH (0.04 M), HOAc (5 eq.) and tert-butyl[(3-{methyl[2-(methylamino)ethyl]amino}propyl)sulfonyl]carbamate (2 eq. Example 15, steps 1-3) were added followed by Et3N (3 eq.) and the mixture was stirred for 5 min. NaCNBH3 (2 eq.) was added and the mixture was stirred for 18 h. All volatiles were evaporated and the residual material was dissolved in EtOAc. The solution was extracted with sat. aq. NaHCO3, water and brine. After drying over Na2SO4 all volatiles were evaporated in vacuo and the compound was used without purification in the next reaction. (ES) m/z 697 (M+H)+.

後処理

  1. stirringthe mixture was stirred for 18 h
  2. customAll volatiles were evaporated
  3. dissolutionthe residual material was dissolved in EtOAc
  4. extractionThe solution was extracted with sat. aq. NaHCO3, water and brine
  5. dry with materialAfter drying over Na2SO4 all volatiles
  6. customwere evaporated in vacuo
  7. customthe compound was used without purification in the next reaction

出典と根拠

ORDレコード
ord-8784ee27327b466594d63f005d989929
出典データセット
uspto-grants-2012_01
特許番号
US08101595B2

反応ノート

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