Triethylamine → HCID 58979258, compound

HRID 1181076Notes

Reaction equation

HRID 1181076 reaction equation
[C:1]([O:5][C:6](=[O:33])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30][NH:31][CH3:32])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:41][C:42]1[S:43][C:44]([Cl:50])=[CH:45][C:46]=1[C:47](Cl)=[O:48]>C(Cl)Cl.CCOC(C)=O>[C:1]([O:5][C:6](=[O:33])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30][N:31]([C:47]([C:46]1[CH:45]=[C:44]([Cl:50])[S:43][C:42]=1[Cl:41])=[O:48])[CH3:32])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27770842,5-Dichlorothiophene-3-carbonyl chlorideHCID 58978946HCID 58978946, compound

Product 1

HCID 58979258HCID 58979258, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-{2-methylaminomethyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid tert-butyl ester (37 mg, 0.083 mmol) in CH2Cl2 (5 mL) was treated with triethylamine (0.035 mL, 0.25 mmol) then 2,5-dichloro-thiophene-3-carbonyl chloride (0.054 mL, 0.25 mmol) and stirred at ambient temperature overnight. The mixture was diluted with EtOAc (25 mL) and washed with brine (3×10 mL). The organic layer was dried (Na2SO4) and concentrated to the title compound (50 mg, 96%). MS (ES) m/z 629, 631 [M+1].

Workup

  1. washwashed with brine (3×10 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated to the title compound (50 mg, 96%)

Sources & evidence

ORD record
ord-f2e9f1d2ada24028a0fddb31fcd4e475
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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