Triethylamine → HCID 90010412, compound

HRID 706786Notes

Reaction equation

HRID 706786 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].Cl[C:18]([C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1)=[O:19]>C(#N)C.ClCCl>[C:14]([C:10]1[N:9]([NH:8][C:18]([C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=2)=[O:19])[CH:13]=[CH:12][CH:11]=1)(=[O:15])[NH2:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 104191801-Amino-1H-pyrrole-2-carboxamide

Product 1

HCID 90010412HCID 90010412, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (554 μl, 4.00 mmol) is added to a suspension of 1-amino-1H-pyrrole-2-carboxylic acid amide (501 mg, 4.00 mmol) in acetonitrile (8.0 ml). Then a suspension of methyl 4-chlorocarbonylbenzoate (264 μl, 2.00 mmol) in dichloromethane (4.0 ml) is added slowly. The reaction mixture is stirred at room temperature for 18 hours. The solvents are evaporated and the residue is triturated with water. The solid is filtered off, washed with water and dried under vacuum to give methyl 4-[(2-carbamoylpyrrol-1-yl)carbamoyl]benzoate as white crystals; HPLC/MS 1.45 min (C), [M+H] 288.

Workup

  1. additionis added slowly
  2. customThe solvents are evaporated
  3. customthe residue is triturated with water
  4. filtrationThe solid is filtered off
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-a6d965d004cb4af18aef120133e3e065
Source dataset
uspto-grants-2015_11
Patent number
US09174995B2

Reaction notes

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