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 421967Notes

Reaction equation

HRID 421967 reaction equation
[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

Participants

7

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-8784ee27327b466594d63f005d989929
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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