Lithium Hydroxide → HCID 68627117, compound

HRID 1408482Notes

Reaction equation

HRID 1408482 reaction equation
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([O:23]C)=[O:22])=[CH:18][CH:19]=3)[N:14]=[CH:13][N:12]=2)=[CH:6][CH:5]=1.[Li+].[OH-]>C1COCC1.O>[F:26][C:2]([F:1])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([OH:23])=[O:22])=[CH:18][CH:19]=3)[N:14]=[CH:13][N:12]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68626825HCID 68626825, compound

Product 1

HCID 68627117HCID 68627117, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 4-(4-(trifluoromethoxy)phenylamino)quinazoline-7-carboxylate (156 mg, 0.43 mmol), LiOH (25.5 mg, 1.07 mmol) was dissolved in THF (4 ml) and H2O (1 mL). The mixture was stirred at 60° C. for 3 h. Acidified with acetic acid resulted brown solid which was collected by filtration. It was then dried in vacuo and used for the next step without any further purification (120 mg, 80% Yield). 1H NMR 400 MHz (DMSO-d6) δ 12.25 (s, 1H), 10.12 (s, 1H), 8.68 (s, 1H), 8.65 (d, 1H, J=1.6 Hz), 8.20-8.11 (m, 2H), 8.02 (d, 2H, J=8.8 Hz), 7.42 (d, 2H, J=8.8 Hz. MS m/z 350.1 (M+1).

Workup

  1. filtrationAcidified with acetic acid resulted brown solid which was collected by filtration
  2. customIt was then dried in vacuo
  3. customused for the next step without any further purification (120 mg, 80% Yield)

Sources & evidence

ORD record
ord-c225f985dc7543beab3fbb237b5348b5
Source dataset
uspto-grants-2014_12
Patent number
US08921336B2

Reaction notes

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