Triethylamine → Methyl 4-{2-[(benzofuran-2-yl-carbonyl)amino]ethylsulfanyl}benzoate

HRID 1173808Notes

Reaction equation

HRID 1173808 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1.[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]1[C:25](O)=[O:26].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]1[C:25]([NH:2][CH2:3][CH2:4][S:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1)=[O:26]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10331Benzofuran-2-carboxylic acidHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66687893Methyl 4-(2-aminoethylsulfanyl)benzoate hydrochloride

Product 1

HCID 66687946Methyl 4-{2-[(benzofuran-2-yl-carbonyl)amino]ethylsulfanyl}benzoateYield 38.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 4-(2-aminoethylsulfanyl)benzoate hydrochloride (0.248 g, 1.00 mmol), was combined with benzofuran-2-carboxylic acid (0.162 g, 1.00 mmol) and HBTU (0.379 g, 1.00 mmol) in DMF (5 ml) at room temperature. Triethylamine (0.307 ml, 2.2 mmol) was added and the reaction mixture was stirred at room temperature overnight. Saturated aqueous NaHCO3 (15 ml) was added to give precipitates which was broken up by the addition of water (20 ml). The solid was filtered and the cake was dissolved in ethyl acetate. The residual water was removed by pipette and hexane was added to give methyl 4-{2-[(benzofuran-2-yl-carbonyl)-amino]ethylsulfanyl}benzoate (0.138 g) as a gum which was used in the next step without further purification.

Workup

  1. customto give
  2. customprecipitates which
  3. additionwas broken up by the addition of water (20 ml)
  4. filtrationThe solid was filtered
  5. dissolutionthe cake was dissolved in ethyl acetate
  6. customThe residual water was removed by pipette and hexane
  7. additionwas added

Sources & evidence

ORD record
ord-c6dbdd8e88f1469bacbed526e04a88c7
Source dataset
uspto-grants-2010_11
Patent number
US07834054B2

Reaction notes

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