Hydrochloric Acid → HCID 66675181, compound

HRID 421964Notes

Reaction equation

HRID 421964 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:45]([O:47]C)=[O:46])=[CH:12][C:13]=3[N:14]3[CH2:20][CH:19]([N:21]([CH3:40])[CH2:22][CH2:23][N:24]([CH3:39])[CH2:25][CH2:26][CH2:27][S:28](=[O:38])(=[O:37])[NH:29]C(=O)OC(C)(C)C)[CH2:18][C:17]4[CH:41]=[CH:42][CH:43]=[CH:44][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+].Cl>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:29][S:28]([CH2:27][CH2:26][CH2:25][N:24]([CH3:39])[CH2:23][CH2:22][N:21]([CH3:40])[CH:19]1[CH2:18][C:17]2[CH:41]=[CH:42][CH:43]=[CH:44][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:45]([OH:47])=[O:46])=[CH:12][C:13]=3[N:14]2[CH2:20]1)(=[O:38])=[O:37]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 66674694HCID 66674694, compound

Product 1

HCID 66675181HCID 66675181, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Conditions

Temperature
65 °C

Procedure

Methyl 13-cyclohexyl-6-[methyl(3,11,11-trimethyl-7,7-dioxido-9-oxo-10-oxa-7-thia-3,8-diazadodec-1-yl)amino]-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate was dissolved in DCM/TFA 3:1 (0.03M) and the mixture was left standing at RT. After 45 min all volatiles were evaporated in vacuo. The residue was dissolved in MeOH (0.07M) and 1M aqueous KOH solution (9 eq.) was added. The mixture was stirred at 65° C. for 4h. After cooling to 0° C. the pH of the solution was adjusted with 1 M 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. (ES+) m/z 567 (M+H)+.

Workup

  1. waitthe mixture was left
  2. customstanding at RT
  3. customAfter 45 min all volatiles were evaporated in vacuo
  4. dissolutionThe residue was dissolved in MeOH (0.07M)
  5. temperatureAfter cooling to 0° C. the pH of the solution
  6. extractionThe resulting suspension was extracted with EtOAc
  7. washThe combined organic phases were washed with brine
  8. dry with materialdried over Na2SO4
  9. customAll volatiles were evaporated in vacuo
  10. customThe residual material was used without further purification in the next reaction

Sources & evidence

ORD record
ord-032434f74dc345c69785549f2447b234
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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