Butyric Acid → HCID 56597053, compound

HRID 2046162Notes

Reaction equation

HRID 2046162 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[C:28]3[C:23]([CH2:24][CH2:25][C:26](=[O:36])[N:27]3[C:30]([O:32][CH:33](Cl)[CH3:34])=[O:31])=[CH:22][CH:21]=2)[CH2:11][CH2:10]1.[C:37]([OH:42])(=[O:41])[CH2:38][CH2:39][CH3:40].C(N(C(C)C)C(C)C)C>C(OCC)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:29]=[C:28]3[C:23]([CH2:24][CH2:25][C:26](=[O:36])[N:27]3[C:30]([O:32][CH:33]([O:41][C:37](=[O:42])[CH2:38][CH2:39][CH3:40])[CH3:34])=[O:31])=[CH:22][CH:21]=2)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 264Butyric AcidHCID 81531DiisopropylethylamineHCID 66810209HCID 66810209, compound

Product 1

HCID 56597053HCID 56597053, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-chloroethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate (2.0 g, 3.60 mmol) was stirred with butyric acid (1.0 mL, 10.81 mmol) and ethyldiisopropylamine (0.94 mL, 5.41 mmol) at 50° C. for 48 hours. The reaction was diluted with diethyl ether (20 mL) and quenched with aqueous saturated NaHCO3 (40 mL). The reaction was extracted with ethyl acetate (2×50 mL) and the combined organics were washed with water (50 mL), brine (50 mL) then dried (MgSO4). The crude product was purified by column chromatography on silica eluting with 0.5% Et3N/ethyl acetate to give 1-(butyryloxy)ethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate, Compound-90 (628 mg, 23% over 2 steps).

Workup

  1. customquenched with aqueous saturated NaHCO3 (40 mL)
  2. extractionThe reaction was extracted with ethyl acetate (2×50 mL)
  3. washthe combined organics were washed with water (50 mL), brine (50 mL)
  4. dry with materialthen dried (MgSO4)
  5. customThe crude product was purified by column chromatography on silica eluting with 0.5% Et3N/ethyl acetate

Sources & evidence

ORD record
ord-fc999b093f0c4cb889a0f156d21c43ab
Source dataset
uspto-grants-2013_11
Patent number
US08592427B2

Reaction notes

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