Acetic Acid → HCID 67235714, compound

HRID 1748312Notes

Reaction equation

HRID 1748312 reaction equation
[CH3:1][CH:2]1[CH2:20][CH2:19][N:6]2[C:7]3[CH:8]=[C:9]([C:14]([O:16]CC)=[O:15])[CH:10]=[CH:11][C:12]=3[CH:13]=[C:5]2[C:4](=[O:21])[NH:3]1.[OH-].[Na+].C(O)(=O)C.O>C(O)C>[CH3:1][CH:2]1[CH2:20][CH2:19][N:6]2[C:7]3[CH:8]=[C:9]([C:14]([OH:16])=[O:15])[CH:10]=[CH:11][C:12]=3[CH:13]=[C:5]2[C:4](=[O:21])[NH:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 67235121HCID 67235121, compound

Product 1

HCID 67235714HCID 67235714, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 3-methyl-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylate (120 mg, 0.42 mmol) in ethanol (10 mL) is added 1M NaOH solution (1.0 mL, 1.0 mmol). The reaction mixture is heated at 80° C. for 2 h. Acetic acid (3 mL) is and water (60 mL) are added and the mixture is concentrated. The residue is purified by preparative HPLC to afford the title compound (63 mg, 58%).

Workup

  1. concentrationthe mixture is concentrated
  2. customThe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-1d2c76b40bea4a8a8ca981a00906d4a8
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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