Triethylamine → HCID 90010296, compound

HRID 706784Notes

Reaction equation

HRID 706784 reaction equation
C(N(CC)CC)C.[NH2:8][N:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]([NH2:16])=[O:15].[CH3:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1>C(#N)C.ClCCl>[CH3:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH:8][N:9]2[CH:13]=[CH:12][CH:11]=[C:10]2[C:14]([NH2:16])=[O:15])=[O:23])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 104191801-Amino-1H-pyrrole-2-carboxamide

Product 1

HCID 90010296HCID 90010296, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (277 μl, 2.00 mmol) is added to a suspension of 1-amino-1H-pyrrole-2-carboxylic acid amide (250 mg, 2.00 mmol) in acetonitrile (4.0 ml). Under external cooling with ice, a solution of 4-methylbenzoyl chloride (264 μl, 2.00 mmol) in dichloromethane (0.6 ml) is added dropwise. The reaction mixture is stirred at room temperature for 18 hours. The solvents are evaporated and the residue is taken up in dichloromethane and saturated NaHCO3 solution. A precipitate forms which is filtered off, washed with water and dried under vacuum to give 1-(4-methyl-benzoylamino)-1H-pyrrole-2-carboxylic acid amide as white crystals; HPLC/MS 1.57 min (A), [M+H] 244;

Workup

  1. temperatureUnder external cooling with ice
  2. customThe solvents are evaporated
  3. filtrationA precipitate forms which is filtered off
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f1216a01c70a4225a9af985f430cc83e
Source dataset
uspto-grants-2015_11
Patent number
US09174995B2

Reaction notes

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