Triethylamine → HCID 135445242, compound

HRID 2262768Notes

Reaction equation

HRID 2262768 reaction equation
[CH3:1][N:2]([CH3:35])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)=[O:19])=[C:13]([C:31](=[NH:34])[NH:32][NH2:33])[CH:12]=2)=[CH:7][CH:6]=1)=[O:4].C(N(CC)CC)C.Cl[C:44](Cl)([O:46]C(=O)OC(Cl)(Cl)Cl)Cl.C(=O)(O)[O-].[Na+]>ClCCl.O>[CH3:1][N:2]([CH3:35])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)=[O:19])=[C:13]([C:31]3[NH:34][C:44](=[O:46])[NH:33][N:32]=3)[CH:12]=2)=[CH:7][CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 178484430HCID 178484430, compound

Product 1

HCID 135445242HCID 135445242, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3′-(N-aminocarbamimidoyl)-4′-[3-(3-trifluoromethyl-phenyl)-ureido]-biphenyl-4-carboxylic acid dimethylamide (322 mg) and triethylamine (212 microliters) dissolved in dichloromethane (5 ml) at -50° C. was treated with a solution of triphosgene (236 mg) in dichloromethane (5 ml). The mixture was stirred for 2.5 hrs at ambient temperature and poured into water. After adjusting to pH 7 with aq. sodium bicarbonate, the mixture was extracted with EtOAc. The organic layers were dried over Na2SO4, filtered and concentrated. Column chromatography on silica afforded 3′-(5-Oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl)-4′-[3-(3-trifluromethyl-phenyl)-ureido]-biphenyl-4-carboxylic acid dimethylamide as a white solid. Mp.=212° C.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dc5a44caa2494b31843627a4114337b1
Source dataset
uspto-grants-2010_12
Patent number
US07851492B2

Reaction notes

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