Ammonia → N-(2-amino-2-oxoethyl)-5-chloro-1H-indole-2-carboxamide

HRID 651165Notes

Reaction equation

HRID 651165 reaction equation
CO[C:3](=[O:18])[CH2:4][NH:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([Cl:17])=[CH:12][CH:11]=2)=[O:7].[NH3:19]>CO>[C:3]([CH2:4][NH:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([Cl:17])=[CH:12][CH:11]=2)=[O:7])(=[O:18])[NH2:19]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 4893740methyl N-[(5-chloro-1H-indol-2-yl)carbonyl]glycinate

Product 1

HCID 4028518N-(2-amino-2-oxoethyl)-5-chloro-1H-indole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[(5-Chloro-1H-indole-2-carbonyl)-amino]-acetic acid methyl ester (100 mg, 0.40 mmol) was added to a saturated solution of ammonia in methanol (ca. 3 mL) at 25° C. The suspension was sonicated for 1 hour and the resulting solution concentrated. The residue was triturated with ether/hexanes and dried. Yield 77 mg, 77%; HPLC (60/40) 2.78 minutes (98%); PBMS 252/254 (MH+, 100%);

Workup

  1. customThe suspension was sonicated for 1 hour
  2. concentrationthe resulting solution concentrated
  3. customThe residue was triturated with ether/hexanes
  4. customdried
  5. customHPLC (60/40) 2.78 minutes (98%)

Sources & evidence

ORD record
ord-f94a54465e9d4d12beddd5a8eaf8728d
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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