Diisopropylethylamine → HCID 67017630, compound

HRID 2243172Notes

Reaction equation

HRID 2243172 reaction equation
[S:1]1[C:5]([C:6]([OH:8])=O)=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[Cl:13][C:14]1[CH:15]=[C:16]([CH2:21][CH2:22][NH2:23])[CH:17]=[CH:18][C:19]=1[Cl:20].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[Cl:13][C:14]1[CH:15]=[C:16]([CH2:21][CH2:22][NH:23][C:6]([C:5]2[S:1][C:2]3[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=3[CH:4]=2)=[O:8])[CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 95864Benzo(b)thiophene-2-carboxylic acidHCID 2179583,4-DichlorophenethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 67017630HCID 67017630, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 300 mg (1.68 mmol) of benzo[b]thiophene-2-carboxylic acid in DMF (8 ml) were added 320 mg (1.68 mmol) of 2-(3,4-dichloro-phenyl)-ethylamine and 595 mg (1.85 mmol) of TBTU. After 10 min 1.47 ml (8.42 mmol) of N,N-diisopropylethyl amine were added and the reaction mixture was stirred over night at RT. Then water was added and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with water, brine, sat. NaHCO3 solution, 1N HCl and again with brine. The organic layer was then dried (MgSO4) and concentrated. The remaining residue was purified by column chromatography (silica gel; ethyl acetate/cyclohexane 9:1) to yield 515 mg (87%) of benzo[b]thiophene-2-carboxylic acid[2-(3,4-dichloro-phenyl)-ethyl]-amide as a white solid. MS (ISP) 350.2 (M+H)+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic extracts were washed with water, brine, sat. NaHCO3 solution, 1N HCl and again with brine
  3. dry with materialThe organic layer was then dried (MgSO4)
  4. concentrationconcentrated
  5. customThe remaining residue was purified by column chromatography (silica gel; ethyl acetate/cyclohexane 9:1)

Sources & evidence

ORD record
ord-e58689368b384e9fb14ec08a28be62a3
Source dataset
uspto-grants-2010_03
Patent number
US07674815B2

Reaction notes

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