Triethylamine → HCID 140490343, compound

HRID 31502Notes

Reaction equation

HRID 31502 reaction equation
Cl.[C:2]([C:5]1[CH:6]=[CH:7][C:8]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:9]([CH2:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:22])=[C:17]([CH3:28])[CH:16]=2)=[O:13])[CH:10]=1)(=[NH:4])[NH2:3].C(N(CC)CC)C.[N+](C1C=CC([C:53]2[CH:61]=[CH:60][CH:59]=[CH:58][C:54]=2[C:55]([O-])=[O:56])=CC=1)([O-])=O>C(Cl)Cl>[C:55]([NH:4][C:2]([C:5]1[CH:6]=[CH:7][C:8]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[C:9]([CH2:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:22])=[C:17]([CH3:28])[CH:16]=2)=[O:13])[CH:10]=1)=[NH:3])(=[O:56])[C:54]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:53]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 17937121HCID 17937121, compoundHCID 69308209HCID 69308209, compound

Product 1

HCID 140490343HCID 140490343, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

350 mg (0.69 mmol) of 2-(5-carbamimidoyl-2-benzyloxy-phenyl)-N-[3-methyl-4-(pyrrolidin-1-yl-carbonyl)-phenyl]-acetamide-hydrochloride are suspended in 40 ml of methylene chloride and combined with 1.0 ml of triethylamine and 300 mg (1.3 mmol) of 4-nitrophenylbenzoate. The reaction mixture is refluxed for 4 hours. After the addition of 100 ml of saline solution the aqueous phase is extracted 3× with methylene chloride. The combined organic phases are dried over sodium sulphate and concentrated by evaporation.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. additionAfter the addition of 100 ml of saline solution the aqueous phase
  3. extractionis extracted 3× with methylene chloride
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-e10f418a412f4efbb5136092bf7f6788
Source dataset
uspto-grants-2008_09
Patent number
US07425641B2

Reaction notes

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