Dimethylformamide → HCID 59654766, compound

HRID 1716982Notes

Reaction equation

HRID 1716982 reaction equation
[C:1]1([C:7]2[O:11][C:10]([C:12]([OH:14])=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]([O:18][C:19]1C=CC(N)=C[C:20]=1CC)(=[O:17])[CH3:16].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:39]2[N:40]=[CH:41][CH:42]=[CH:43][C:38]=2N=N1.[CH3:52]N(C)C=O>>[CH2:19]([O:18][C:15](=[O:17])[CH2:16][C:38]1[CH:39]=[CH:52][C:41]([NH:40][C:12]([C:10]2[O:11][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][CH:9]=2)=[O:14])=[CH:42][CH:43]=1)[CH3:20]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7362555-Phenylfuran-2-carboxylic 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 59654766HCID 59654766, compound

Procedure

Diispropylethylamine (300 μl) was added to a stirred solution of 5-phenyl-furan-2-carboxylic acid (73.5 mg, 0.39 mmol) and ethyl-4-aminophenyl acetate (70 mg, 0.39 mmoles) in N,N-dimethylformamide (10 ml). O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (200 mg, 0.52 mmoles) was added and the solution was stirred at room temperature for 72 hours. The solvent was evaporated, the residue was dissolved in dichloromethane and washed with water, 10% aqueous sodium carbonate, 1 M aqueous hydrochloric acid and finally dried (MgSO4). After evaporation of the solvent, the residue was triturated with cyclohexane and dried to afford (1) (82 mg) as a gum. LC/MS System A; Rt=3.80 mins, m/z (ES+)=350 (M+H for C21H19NO4).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water, 10% aqueous sodium carbonate, 1 M 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-226de33d09e346cab4c823cc5f065a84
Source dataset
uspto-grants-2010_09
Patent number
US07803841B2

Reaction notes

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