Butyric Acid → HCID 178439967, compound

HRID 1985653Notes

Reaction equation

HRID 1985653 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]([F:26])([F:25])[F:24])=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[NH2:8].[C:27](O)(=O)[CH2:28][CH2:29][CH3:30]>O=P(Cl)(Cl)Cl>[CH2:28]([C:27]1[NH:8][C:7]2[CH:6]=[CH:5][C:4]([N:9]3[CH2:10][CH2:11][N:12]([C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[C:23]([F:26])([F:25])[F:24])=[O:16])[CH2:13][CH2:14]3)=[CH:3][C:2]=2[N:1]=1)[CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 264Butyric AcidHCID 66863203HCID 66863203, compound

Product 1

HCID 178439967HCID 178439967, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of [4-(3,4-diaminophenyl)piperazin-1-yl](2-trifluoromethylphenyl)-methanone (0.500 g, 1.370 mmol) and butyric acid (0.180 g, 2.040 mmol) was heated to reflux in POCl3 for 12 h. The mixture was cooled to room temperature and then concentrated. The black syrup was poured over 10% Na2CO3 solution, then extracted with ethyl acetate, washed with water and brine. The solvent was removed in vacuo and the residue was purified by column chromatography to yield the title compound as a yellow syrup in 52% yield (0.115 g). 1H NMR (300 MHz, CDCl3) δ 8.90 (br., s, 1H), 7.69 (d, J=7.6 Hz, 1H), 7.62-7.42 (m, 2H), 7.36 (d, J=9.2 Hz, 2H), 6.98 (s, 1H), 6.87 (dd, J=2.0, 8.7 Hz, 1H), 4.01-3.91 (m, 2H), 3.33 (t, J=4.8 Hz, 2H), 3.15 (t, J=4.8 Hz, 2H), 3.05-2.95 (m, 2H), 2.79 (t, J=7.4 Hz, 2H), 1.85-1.70 (m, 2H), 0.90 (t, J=7.3 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ 167.5, 155.4, 147.2, 134.5, 134.5, 132.3, 129.3, 127.2, 127.0, 126.8, 126.8, 126.7, 126.7, 126.6, 126.2, 125.4, 121.8, 114.7, 102.5, 102.4, 102.3, 51.4, 51.2, 47.3, 41.9, 31.1, 21.6, 13.8. MS (ES+) m/z 417.1 (M+1).

Workup

  1. temperaturewas heated
  2. concentrationconcentrated
  3. additionThe black syrup was poured over 10% Na2CO3 solution
  4. extractionextracted with ethyl acetate
  5. washwashed with water and brine
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c7d50eb49b4d45db9cb5093e393914f8
Source dataset
uspto-grants-2009_06
Patent number
US07547698B2

Reaction notes

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