Acetic Acid → 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

HRID 421962노트

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HRID 421962 반응식
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:28]([O:30][CH3:31])=[O:29])=[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]([CH:26]=O)[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(O)=O.[C:36]([O:40][C:41](=[O:55])[NH:42][S:43]([CH2:46][CH2:47][CH2:48][N:49]([CH3:54])[CH2:50][CH2:51][NH:52][CH3:53])(=[O:45])=[O:44])([CH3:39])([CH3:38])[CH3:37].[BH3-]C#N.[Na+]>CO>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:28]([O:30][CH3:31])=[O:29])=[CH:12][C:13]=3[N:14]3[C:20]=2[C:19]2[CH:18]=[CH:24][CH:23]=[CH:22][C:21]=2[N:17]([CH3:25])[CH:16]([CH2:26][N:52]([CH3:53])[CH2:51][CH2:50][N:49]([CH3:54])[CH2:48][CH2:47][CH2:46][S:43](=[O:44])(=[O:45])[NH:42][C:41](=[O:55])[O:40][C:36]([CH3:39])([CH3:37])[CH3:38])[CH2:15]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 86627899Methyl 13-cyclohexyl-6-formyl-5-methyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-10-carboxylateHCID 86640308Tert-butyl[(3-{methyl[2-(methylamino)ethyl]amino}propyl)sulfonyl]carbamate

생성물 1

HCID 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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Methyl 13-cyclohexyl-6-formyl-5-methyl-6,7-dihydro-5H-indolo[1,2-d][1,4]benzodiazepine-10-carboxylate was dissolved in MeOH (0.08 M) and HOAc was added. Tert-butyl[(3-{methyl[2(methylamino)ethyl]amino}propyl)sulfonyl]carbamate (1.5 eq. prepared as described in Example 15, Steps 1-3) was added and the mixture was stirred for 5 min. NaCNBH3 (1.5 eq.) was added and the mixture was stirred for 6 h. All volatiles were evaporated and the residual material was dissolved in EtOAc. The solution was extracted with sat. aq. NH4Cl, sat. aq. NaHCO3 and brine. After drying over Na2SO4 all volatiles were evaporated in vacuo. A yellow amorphous solid was obtained which was used without further purification in the next reaction (60%). (ES+) m/z 711 (M+H)+.

후처리

  1. stirringthe mixture was stirred for 6 h
  2. customAll volatiles were evaporated
  3. dissolutionthe residual material was dissolved in EtOAc
  4. extractionThe solution was extracted with sat. aq. NH4Cl, sat. aq. NaHCO3 and brine
  5. dry with materialAfter drying over Na2SO4 all volatiles
  6. customwere evaporated in vacuo
  7. customA yellow amorphous solid was obtained which
  8. customwas used without further purification in the next reaction (60%)

출처 및 근거

ORD 기록
ord-01d44d400a4c43debd3720d48fdf5fd0
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101595B2

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