Formamide → HCID 178497210, compound

HRID 1916292Notes

Reaction equation

HRID 1916292 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:15]([O:17]CC)=O)=[C:10]([NH2:14])[NH:11]2)=[CH:7][CH:6]=1)=[O:4].C([O-])=O.[NH4+].O.[CH:25]([NH2:27])=O>>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]3[C:15]([OH:17])=[N:27][CH:25]=[N:14][C:10]=3[NH:11]2)=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 4

HCID 713FormamideHCID 962WaterHCID 2723923Ammonium formateHCID 59447961HCID 59447961, compound

Product 1

HCID 178497210HCID 178497210, compound

Conditions

Temperature
170 °C

Procedure

A suspension of 2-amino-1H-indole-3,6-dicarboxylic acid 3-ethyl ester 6-methyl ester (259 mg, 1 mmol) and ammonium formate (62 mg, 1 mmol) in 2 mL formamide was heated under an atmosphere of nitrogen to 170° C. overnight. On cooling to room temperature, water was added and the resulting precipitate was collected by filtration and dried in a vacuum oven for 4 hours to a constant weight to give the title compound (103 mg, 0.42 mmol). LC-MS (1) Rt 1.27 min; m/z (ES−) 242.

Workup

  1. temperatureOn cooling to room temperature
  2. filtrationthe resulting precipitate was collected by filtration
  3. customdried in a vacuum oven for 4 hours to a constant weight

Sources & evidence

ORD record
ord-6949e462b7d342f1be77c0970791c894
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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