Diisopropylethylamine → HCID 59773102, compound

HRID 2099541Notes

Reaction equation

HRID 2099541 reaction equation
[CH:1](N(C(C)C)CC)(C)C.[CH3:10][C:11]1[O:12][C:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:14][C:15]=1[C:16]([OH:18])=O.[C:25]([O:28][C:29]1C=CC(N)=C[C:30]=1CC)(=[O:27])[CH3:26].CN(C(ON1N=N[C:48]2[CH:49]=[CH:50][CH:51]=[N:52][C:47]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[CH2:29]([O:28][C:25](=[O:27])[CH2:26][C:48]1[CH:47]=[CH:1][C:51]([NH:52][C:16]([C:15]2[CH:14]=[C:13]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:12][C:11]=2[CH3:10])=[O:18])=[CH:50][CH:49]=1)[CH3:30]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 7365162-Methyl-5-phenyl-3-furoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 53958485HCID 53958485, compound

Product 1

HCID 59773102HCID 59773102, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diisopropylethylamine (427 mg) was added to a stirred solution of 2-methyl-5-phenyl-furan-3-carboxylic acid (334 mg, 1.6 mmol) and ethyl-4-aminophenyl acetate (296 mg, 1.65 mmoles) in N,N-dimethylformamide (30 ml). 0-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (628 mg, 1.65 mmoles) was added and the solution was stirred at room temperature for 18 hours. The solvent was evaporated, the residue was dissolved in dichloromethane and washed with water, 10% aqueous sodium carbonate, 1M aqueous hydrochloric acid and finally dried (MgSO4). After evaporation of the solvent, the residue was triturated with cyclohexane and dried to afford (4-[(2-Methyl-5-phenyl-furan-3-carbonyl)-amino]-phenyl}-acetic acid ethyl ester (1)(466 mg) as a gum. LC/MS System D; Rt=10.64 mins, m/z (ES+)=364 (M+H for C22H21NO4).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water, 10% aqueous sodium carbonate, 1M aqueous hydrochloric acid
  4. dry with materialfinally dried (MgSO4)
  5. customAfter evaporation of the solvent
  6. customthe residue was triturated with cyclohexane
  7. customdried

Sources & evidence

ORD record
ord-9bd52e58561d464d9a9bf6e0f2420657
Source dataset
uspto-grants-2009_08
Patent number
US07569602B2

Reaction notes

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