Hydrochloric Acid → HCID 178518050, compound

HRID 1916300Notes

Reaction equation

HRID 1916300 reaction equation
C(O[C:4]([C:6]1[C:14]2[C:9](=[CH:10][N:11]=[CH:12][CH:13]=2)[NH:8][C:7]=1[NH2:15])=[O:5])C.C([O-])=O.[NH4+].Cl.[CH:21]([NH2:23])=O>>[N:15]1[C:7]2[NH:8][C:9]3[CH:10]=[N:11][CH:12]=[CH:13][C:14]=3[C:6]=2[C:4]([OH:5])=[N:23][CH:21]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 713FormamideHCID 2723923Ammonium formateHCID 59447939HCID 59447939, compound

Product 1

HCID 178518050HCID 178518050, compound

Conditions

Temperature
170 °C

Procedure

A mixture of 2-Amino-1H-pyrrolo[2,3-c]pyridine-3-carboxylic acid ethyl ester (1.80 g, 8.8 mmol) and ammonium formate (0.62 g, 9.8 mmol) in formamide (10 mL) was heated at 170° C. for 18 hours. 1 M HCl was added to the cooled reaction mixture and the resulting suspension was filtered to remove insolubles. The filtrate was then adjusted to pH 7 with saturated sodium bicarbonate solution. The resulting precipitate was collected by filtration and dried to a constant weight in a vacuum oven to give the title compound (0.74 g, 4.0 mmol). 1H NMR (DMSO) δ 12.5 (s, br), 8.83 (1H, s), 8.37 (1H, d, J=4.0), 8.26 (1H, s), 7.89 (1H, d, J=4.0); LC-MS (1) Rt 0.75 min; m/z 185 (ES−).

Workup

  1. filtrationthe resulting suspension was filtered
  2. customto remove insolubles
  3. filtrationThe resulting precipitate was collected by filtration
  4. customdried to a constant weight in a vacuum oven

Sources & evidence

ORD record
ord-21e1574c3f1b43ae86e00110eb91de23
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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