Hydrochloric Acid → HCID 56655846, compound

HRID 2400435Notes

Reaction equation

HRID 2400435 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:21])=[C:9]([O:12][C:13]3[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:20])[CH:10]=2)[N:5]=[C:4]([N:22]2[CH:26]=[C:25]([C:27]([O:29]CC)=[O:28])[CH:24]=[N:23]2)[N:3]=1.[Li+].[OH-].Cl>C1COCC1>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:21])=[C:9]([O:12][C:13]3[C:14]([CH3:20])=[CH:15][CH:16]=[CH:17][C:18]=3[CH3:19])[CH:10]=2)[N:5]=[C:4]([N:22]2[CH:26]=[C:25]([C:27]([OH:29])=[O:28])[CH:24]=[N:23]2)[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86686096HCID 86686096, compound

Product 1

HCID 56655846HCID 56655846, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 1-[4-amino-6-(2,6-dimethyl-phenoxy)-7-fluoro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid, ethyl ester (65 mg, 0.15 mmol), 1M aqueous LiOH (1.5 mL, 1.5 mmol), and THF (3 mL) was heated to 40° C. for 16 h with rapid stirring. The mixture was then cooled in an ice bath, and 1M HCl (1.5 mL, 1.5 mmol) was added. The resulting precipitate was collected by filtration, washed with water, and dried to furnish the titled compound (45 mg, 74%). MS (ESI): mass calcd. for C20H16FN5O3, 393.1; m/z found, 394.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 12.72 (s, 1H), 8.91 (d, J=0.7 Hz, 1H), 8.42-7.98 (m, 3H), 7.70 (d, J=11.9 Hz, 1H), 7.37 (d, J=9.0 Hz, 1H), 7.25-7.20 (m, 2H), 7.17 (dd, J=8.6, 6.2 Hz, 1H), 2.12 (s, 6H).

Workup

  1. temperatureThe mixture was then cooled in an ice bath
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-e3e9b4135977414a9c2ca69d384ab822
Source dataset
uspto-grants-2014_08
Patent number
US08796263B2

Reaction notes

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