Hydrochloric Acid → HCID 57473415, compound

HRID 1987504Notes

Reaction equation

HRID 1987504 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:17]([CH2:18][C:19]3[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=3[C:21]#[N:22])[C:16](=[O:27])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([F:28])[CH:14]=3)[N:9]=2)[CH2:3]1.[OH-:29].[Na+].OO.Cl>C1COCC1>[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:17]([CH2:18][C:19]3[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=3[C:21]([NH2:22])=[O:29])[C:16](=[O:27])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([F:28])[CH:14]=3)[N:9]=2)[CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 57425478HCID 57425478, compound

Product 1

HCID 57473415HCID 57473415, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[2-(3-amino-piperidin-1-yl)-6-fluoro-4-oxo-4H-quinazolin-3-ylmethyl]-benzonitrile (Example 6,50 mg) in 5 mL of THF was added 2 mL of 1N NaOH, followed by 2 mL H2O2. After stirring at room temperature overnight, the mixture was acidified with concentrated HCl. Removal of the solvent and purification by Preparative LC/MS provided the title compound. 1H NMR (400 MHz, MeOD): δ 7.68-7.74 (m, 1H), 7.59-7.66 (m, 1H), 7.48-7.58 (m, 2H), 7.29-7.40 (m, 2H), 7.02 (d, J=6.57 Hz, 1H), 5.58 (AB q, J=22.74, 15.66 Hz, 2H), 3.49-3.59 (m, 2H), 3.17-3.26 (m, 1H), 3.01-3.10 (m, 2H), 1.64-2.09 (m, 4H). MS: (ES) [m+H] calculated for C21H22FN5O2, 396; found 396.

Workup

  1. customRemoval of the solvent and purification by Preparative LC/MS

Sources & evidence

ORD record
ord-7aac7e373da6476a8345df7de6100230
Source dataset
uspto-grants-2009_06
Patent number
US07550590B2

Reaction notes

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