Potassium Carbonate → HCID 178513385, compound

HRID 2036811Notes

Reaction equation

C([C:3]1[N:10]=[CH:9][C:8]([C:11]2[N:20]=[C:19]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:12]=2)=[CH:7][C:4]=1[C:5]#[N:6])C.Cl.[NH2:36][OH:37].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:37][NH:36][C:5](=[NH:6])[C:4]1[CH:7]=[C:8]([C:11]2[N:20]=[C:19]([NH:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[N:12]=2)[CH:9]=[N:10][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)nicotinonitrile (described in Example 6, 0.10 g, 0.24 mmol) in ethanol (5 mL) was added hydroxylamine hydrochloride (0.033 g, 0.48 mmol) and potassium carbonate (0.076 g, 0.72 mmol). The reaction mixture was heated to reflux at 80° C. for 16 h. The ethanol solvent was evaporated under reduced pressure and the residue was dissolved in DCM, and washed with water. The organic layer was dried, filtered and concentrated to provide N-hydroxy-5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)nicotinimidamide (0.2 g) which was used without further purification. LCMS Method X: retention time 1.788 min; [M+1]=448.0.

Workup

temperatureThe reaction mixture was heated
customThe ethanol solvent was evaporated under reduced pressure
dissolutionthe residue was dissolved in DCM
washwashed with water
customThe organic layer was dried
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-5c1dc27b2ae44168bdb48474c45ea96d
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575184B2

Reaction notes

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