Hydrochloric Acid → HCID 70978855, compound

HRID 1485410Notes

Reaction equation

HRID 1485410 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:27](=[O:28])[C:19]3([CH2:21][CH:20]3[C:22]([O:24]CC)=[O:23])[C:14]3=[N:15][N:16]=[C:17]([CH3:18])[N:13]3[C:12]3[CH:29]=[CH:30][CH:31]=[CH:32][C:11]2=3)=[CH:6][CH:5]=1.Cl>CO.O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:27](=[O:28])[C:19]3([CH2:21][CH:20]3[C:22]([OH:24])=[O:23])[C:14]3=[N:15][N:16]=[C:17]([CH3:18])[N:13]3[C:12]3[CH:29]=[CH:30][CH:31]=[CH:32][C:11]2=3)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70979115HCID 70979115, compound

Product 1

HCID 70978855HCID 70978855, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

NaOH (48 mg, 1.2 mmol) was added to a solution of ethyl 6-(4-chlorophenyl)-1-methyl-5-oxo-5,6-dihydrospiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine-4,1′-cyclopropane]-2′-carboxylate (100 mg, 0.24 mmol) in MeOH (10 mL) and water (4 mL). It was stirred at room temperature overnight. The solution was adjust to pH=5 using HCl solution (1 M), then concentrated, adding dichloromethane (5 mL), filtered and the filtrate was concentrated to give crude 6-(4-chlorophenyl)-1-methyl-5-oxo-5,6-dihydrospiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine-4,1′-cyclopropane]-2′-carboxylic acid, which was used in the next step directly. LRMS (M+H)+: 394 m/z.

Workup

  1. concentrationconcentrated
  2. additionadding dichloromethane (5 mL)
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b7b41db736fe471cb044536ff2581289
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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