Dimethylformamide → HCID 10455092, compound

HRID 1823216Notes

Reaction equation

HRID 1823216 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:12]=[C:11]([CH2:22][CH:23]([C:27]3[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=3)C(O)=O)[CH:10]=2)[CH:5]=[CH:6][C:7]=1Cl.[CH:34]1N=CN(C(N2C=NC=C2)=O)C=1.C(=O)([O-])[O-].[NH4+].[NH4+].C[N:53]([CH:55]=[O:56])C>O>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([N:13]2[C:9]([C:4]3[CH:5]=[CH:6][C:7]([CH3:34])=[CH:2][CH:3]=3)=[CH:10][C:11]([CH2:22][CH:23]([C:27]3[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=3)[C:55]([NH2:53])=[O:56])=[N:12]2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 517111Ammonium CarbonateHCID 10096710HCID 10096710, compound2×

Product 1

HCID 10455092HCID 10455092, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-[1-(4-methoxy-phenyl)-5-p-tolyl-1H-pyrazol-3-yl]-2-m-tolyl-propionic acid (product of Method 2) (0.10 g, 0.23 mmol) and CDI (85 mg, 0.52 mmol) in DMF (2.5 mL) was stirred at rt for 30 min. The solution was then cooled to 0° C., and ammonium carbonate (99 mg, 1.0 mmol) was added in portions. The reaction mixture was allowed to warm to rt and stirred for an additional 18 h. The reaction mixture was then diluted with water (25 mL) and extracted with EtOAc (3×25 mL). Organic layers were combined, washed with water (3×25 mL) and brine (1×25 mL) and dried with Na2SO4, and the solvent removed under reduced pressure giving 70 mg (71%) of the title compound. HPLC: Rt=9.38 (Method A). MS (ES+): mass calculated for C27H27N3O2, 425.21; m/z found 426.2 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 7.50 (s, 1H), 7.22 (s, 1H), 7.20 (d, J=5.1 Hz, 2H), 7.14-7.10 (m, 3H), 7.04 (d, J=8.2 Hz, 2H), 6.93 (d, J=9.0 Hz, 2H), 6.82 (s, 1H), 6.27 (s, 1H), 3.89 (dd, J=5.5, 9.6 Hz, 1H), 3.76 (s, 3H), 3.34 (m, 1H), 2.82 (dd, J=5.5, 14.7 Hz, 1H), 2.29 (s, 3H), 2.27 (s, 3H).

Workup

  1. temperatureThe solution was then cooled to 0° C.
  2. temperatureto warm to rt
  3. stirringstirred for an additional 18 h
  4. extractionextracted with EtOAc (3×25 mL)
  5. washwashed with water (3×25 mL) and brine (1×25 mL)
  6. dry with materialdried with Na2SO4
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4bb7a1cc927245f8b162c2a67cccdba9
Source dataset
uspto-grants-2006_05
Patent number
US07037931B2

Reaction notes

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