Formamide → HCID 178509549, compound

HRID 133029Notes

Reaction equation

HRID 133029 reaction equation
C(O[C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[NH:8][C:7]=1[NH2:19])=[O:5])C.[CH3:20][N:21](C=O)C.C(N)=O>C(O)=O>[OH:5][C:4]1[C:6]2[CH:10]=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=3)[NH:8][C:7]=2[N:19]=[CH:20][N:21]=1

Participants

5

Reactant 3

HCID 713FormamideHCID 6228DimethylformamideHCID 691589182-amino-5-(4-cyano-phenyl)-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 178509549HCID 178509549, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 36.6 g (0.143 mol) 2-amino-5-(4-cyano-phenyl)-1H-pyrrole-3-carboxylic acid ethyl ester, 140 ml DMF, 305 ml formamide and 14.6 ml 85% formic acid is heated for 16 h at 150° C. The resulting yellow suspension is cooled to 10° C. and filtered. The solid is washed with methanol (120 ml) and ether (150 ml) and dried. The title compound is obtained as yellowish crystals; m.p.>410° C.; MS-ES+: (M+H)+=254.

Workup

  1. temperatureThe resulting yellow suspension is cooled to 10° C.
  2. filtrationfiltered
  3. washThe solid is washed with methanol (120 ml) and ether (150 ml)
  4. customdried

Sources & evidence

ORD record
ord-45d473beaf11460892f226d5350c323f
Source dataset
uspto-grants-2008_06
Patent number
US07390805B2

Reaction notes

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