Hydrochloric Acid → HCID 56959242, compound

HRID 1854870Notes

Reaction equation

HRID 1854870 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[N:14]2[C:9]([C:10]([CH3:25])=[C:11]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH:12]=[CH:13]2)=[C:8]([CH:26]2[CH2:28][CH2:27]2)[CH:7]=1)=[O:5])C.[Li+].[OH-].Cl.C(OCC)(=O)C>C1COCC1.O>[CH:26]1([C:8]2[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[C:15](=[O:16])[N:14]3[C:9]=2[C:10]([CH3:25])=[C:11]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH:12]=[CH:13]3)[CH2:28][CH2:27]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 86696581HCID 86696581, compound

Product 1

HCID 56959242HCID 56959242, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1-cyclopropyl-8-(4-methoxy-phenyl)-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester (68 mg, 0.180 mmol) in THF (6 mL) and water (2 mL) was treated with LiOH (33 mg, 0.78 mmol). The reaction was heated to 60° C. overnight and acidified with 1N HCl to pH 4. The precipitate was dissolved with ethyl acetate (50 mL) and washed with brine (2×20 mL). The organic phase was separated, dried, and concentrated. The precipitate was filtered to afford the title compound EXAMPLE 47 as yellow solid (22 mg, 35%). ESI-MS m/z: 350 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ ppm: 9.30 (d, J=7.5 Hz, 1H), 8.23 (s, 1H), 7.57 (d, J=7.5 Hz, 1H), 7.52 (d, J=8.4 Hz, 2H), 7.12 (d, J=7.5 Hz, 2H), 3.84 (s, 3H), 2.86 (s, 3H), 2.53-2.51 (m, 1H), 1.06-1.04 (m, 2H), 0.78-0.75 (m, 2H).

Workup

  1. washwashed with brine (2×20 mL)
  2. customThe organic phase was separated
  3. customdried
  4. concentrationconcentrated
  5. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-3c0b11709fc34d4eb94be2976ebfca2c
Source dataset
uspto-grants-2015_02
Patent number
US08962842B2

Reaction notes

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