Triethylamine → 5-{1-[4-(4-Trifluoromethoxy-benzyloxy)-phenyl]-ethylcarbamoyl}-thiophene-2-carboxylic acid methyl ester

HRID 30233

Reaction equation

HRID 30233 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10]([OH:12])=O)=[CH:8][CH:9]=1)=[O:4].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[F:43][C:44]([F:64])([F:63])[O:45][C:46]1[CH:62]=[CH:61][C:49]([CH2:50][O:51][C:52]2[CH:57]=[CH:56][C:55]([CH:58]([NH2:60])[CH3:59])=[CH:54][CH:53]=2)=[CH:48][CH:47]=1>ClCCl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10](=[O:12])[NH:60][CH:58]([C:55]2[CH:56]=[CH:57][C:52]([O:51][CH2:50][C:49]3[CH:61]=[CH:62][C:46]([O:45][C:44]([F:43])([F:63])[F:64])=[CH:47][CH:48]=3)=[CH:53][CH:54]=2)[CH3:59])=[CH:8][CH:9]=1)=[O:4]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 8183525-(Methoxycarbonyl)thiophene-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 586290281-[4-(4-Trifluoromethoxy-benzyloxy)-phenyl]-ethylamine

Product 1

HCID 691351185-{1-[4-(4-Trifluoromethoxy-benzyloxy)-phenyl]-ethylcarbamoyl}-thiophene-2-carboxylic acid methyl esterYield 60.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 160.0 mg (0.859 mmol) thiophene-2,5-dicarboxylic acid monomethyl ester in 25 ml dichloromethane were added 253.0 mg (1.293 mmol) N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride, 175 mg (1.295 mmol) 1-hydroxybenzotriazole hydrate and 130.7 g (1.291 mmol) triethylamine. After 30 min at room temperature 268.0 mg (0.861 mmol) 1-[4-(4-trifluoromethoxy-benzyloxy)-phenyl]-ethylamine were added. The reaction mixture was stirred for 6.5 h. The solvent was evaporated, to the residue was added ethyl acetate and the organic phase was extracted with saturated aqueous NaHCO3 solution and with water. The organic phase was dried over MgSO4 and the solvent was evaporated. The residue was triturated with diisopropyl to provide 249 mg (0.519 mmol) 5-{1-[4-(4-trifluoromethoxy-benzyloxy)-phenyl]-ethylcarbamoyl}-thiophene-2-carboxylic acid methyl ester.

Workup

  1. customThe solvent was evaporated, to the residue
  2. additionwas added ethyl acetate
  3. extractionthe organic phase was extracted with saturated aqueous NaHCO3 solution and with water
  4. dry with materialThe organic phase was dried over MgSO4
  5. customthe solvent was evaporated
  6. customThe residue was triturated with diisopropyl

Sources & evidence

ORD record
ord-63ef497a63904ac69e93e587cc306d69
Source dataset
uspto-grants-2008_09
Patent number
US07423060B2

Linked notes

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