Hydrochloric Acid → 6-{[{2-[[3-(aminosulfonyl)propyl](methyl)amino]ethyl}(methyl)amino]methyl}-13-cyclohexyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

HRID 421968Notes

Reaction equation

HRID 421968 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:46]([O:48]C)=[O:47])=[CH:12][C:13]=3[N:14]3[CH2:20][CH:19]([CH2:21][N:22]([CH3:41])[CH2:23][CH2:24][N:25]([CH3:40])[CH2:26][CH2:27][CH2:28][S:29](=[O:39])(=[O:38])[NH:30]C(=O)OC(C)(C)C)[CH2:18][C:17]4[CH:42]=[CH:43][CH:44]=[CH:45][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O.[OH-].[K+].Cl>C(Cl)Cl>[NH2:30][S:29]([CH2:28][CH2:27][CH2:26][N:25]([CH3:40])[CH2:24][CH2:23][N:22]([CH2:21][CH:19]1[CH2:18][C:17]2[CH:42]=[CH:43][CH:44]=[CH:45][C:16]=2[C:15]2=[C:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:8]3[CH:9]=[CH:10][C:11]([C:46]([OH:48])=[O:47])=[CH:12][C:13]=3[N:14]2[CH2:20]1)[CH3:41])(=[O:39])=[O:38]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 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

Product 1

HCID 666745096-{[{2-[[3-(aminosulfonyl)propyl](methyl)amino]ethyl}(methyl)amino]methyl}-13-cyclohexyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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 was dissolved in DCM (0.1 M) and TFA (44 eq.) was added. After stirring at RT for 1 h all volatiles were evaporated in vacuo and the residual material was coevaporated three times with toluene. (MS (ES+): 595.6). The material was dissolved in MeOH (0.05 M) and 1 M KOH solution (10 eq.) was added and the mixture was stirred at 70° C. for 3 h. After cooling 1N hydrochloric acid was slowly added until neutral pH. The mixture was extracted three times with EtOAc, washed with water and brine. After drying the organic phase over Na2SO4 all volatiles were evaporated in vacuo. The residual material was used without further purification in the next reaction. (ES+) m/z 581 (M+H)+.

Workup

  1. customwere evaporated in vacuo
  2. dissolutionThe material was dissolved in MeOH (0.05 M)
  3. stirringthe mixture was stirred at 70° C. for 3 h
  4. additionwas slowly added until neutral pH
  5. extractionThe mixture was extracted three times with EtOAc
  6. washwashed with water and brine
  7. dry with materialAfter drying the organic phase over Na2SO4 all volatiles
  8. customwere evaporated in vacuo
  9. customThe residual material was used without further purification in the next reaction

Sources & evidence

ORD record
ord-664813e5319649f09f1e2c806ef16147
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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