Hydrochloric Acid → HCID 56960958, compound

HRID 1854852Notes

Reaction equation

HRID 1854852 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:25]([O:27]CC)=[O:26])[C:7](=[O:24])[N:8]3[C:13]=2[C:12]([CH3:14])=[C:11]([C:15]2[CH:20]=[C:19]([CH3:21])[C:18]([NH2:22])=[CH:17][C:16]=2[Cl:23])[CH:10]=[CH:9]3)[CH2:3][CH2:2]1.[Li+].[OH-].Cl.C(OCC)(=O)C>C1COCC1.O>[CH:1]1([C:4]2[CH:5]=[C:6]([C:25]([OH:27])=[O:26])[C:7](=[O:24])[N:8]3[C:13]=2[C:12]([CH3:14])=[C:11]([C:15]2[CH:20]=[C:19]([CH3:21])[C:18]([NH2:22])=[CH:17][C:16]=2[Cl:23])[CH:10]=[CH:9]3)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 86696570HCID 86696570, compound

Product 1

HCID 56960958HCID 56960958, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of ethyl 1-cyclopropyl-8-(4-amino-2-chloro-5-methyl-phenyl)-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (70 mg, 0.171 mmol) in THF (6 mL) and water (2 mL) was treated with LiOH (29 mg, 0.690 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 30 as yellow solid (51 mg, 78%). ESI-MS m/z: 383 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ ppm: 9.28 (d, J=7.5 Hz, 1H), 8.24 (s, 1H), 7.43 (d, J=7.5 Hz, 1H), 6.99 (s, 1H), 6.81 (s, 1H), 5.55 (s, 2H), 2.75 (s, 3H), 2.54-2.52 (m, 1H), 2.07 (s, 3H), 1.03-1.01 (m, 2H), 0.74-0.70 (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-7609b62efe5649be8bf42b6f533ee9f1
Source dataset
uspto-grants-2015_02
Patent number
US08962842B2

Reaction notes

Loading…