Butyric Acid → HCID 56597053, compound

HRID 1518669Notes

Reaction equation

HRID 1518669 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-e087e94be2ac441791172dc95e02c45c
Source dataset
uspto-grants-2015_07
Patent number
US09072788B2

Reaction notes

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