Formamide → HCID 178518049, compound

HRID 1916303Notes

Reaction equation

HRID 1916303 reaction equation
C(O[C:4]([C:6]1[C:10]2[CH:11]=[N:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]=1[NH2:15])=[O:5])C.C([O-])=O.[NH4+].O.[CH:21]([NH2:23])=O>>[N:15]1[C:7]2[NH:8][C:9]3[C:10](=[CH:11][N:12]=[CH:13][CH:14]=3)[C:6]=2[C:4]([OH:5])=[N:23][CH:21]=1

Participants

5

Reactant 4

HCID 713FormamideHCID 962WaterHCID 2723923Ammonium formateHCID 59447959HCID 59447959, compound

Product 1

HCID 178518049HCID 178518049, compound

Conditions

Temperature
175 °C

Procedure

2-Amino-1H-pyrrolo[3,2-c]pyridine-3-carboxylic acid ethyl ester (600 mg, 3 mmol) and ammonium formate (185 mg, 3 mmol) were suspended in 10 mL formamide and heated at 175° C. for 5 hours. Water was added to the cooled reaction mixture and the resulting precipitate collected and dried in vacuo. Unprecipitated product was recovered from the filtrate by using a MP-TsOH SPE cartridge and eluting with 7 N ammonia to give a combined mass of 330 mg of the title compound. LCMS (1): Rt 0.67 min; m/z 188 [M+H]+.

Workup

  1. customthe resulting precipitate collected
  2. customdried in vacuo
  3. customwas recovered from the filtrate
  4. washeluting with 7 N ammonia

Sources & evidence

ORD record
ord-79ddaec2c6ea49238e826a82ab110423
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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