tert-Butanol → HCID 67335525, compound

HRID 1675225Notes

Reaction equation

HRID 1675225 reaction equation
[H-].[Na+].C[C:4]([CH3:7])([OH:6])C.[NH2:8][CH2:9][CH2:10][C:11]([NH:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[N:20]=[CH:19][N:18]=[C:17]2[NH:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=2)=[C:27]([Cl:40])[CH:26]=1)=[O:12]>C1COCC1>[Cl:40][C:27]1[CH:26]=[C:25]([NH:24][C:17]2[C:16]3[C:21](=[CH:22][CH:23]=[C:14]([NH:13][C:11](=[O:12])[CH2:10][CH2:9][NH:8][C:11](=[O:12])[CH2:10][O:6][CH2:4][CH2:7][N:18]([CH3:19])[CH3:17])[CH:15]=3)[N:20]=[CH:19][N:18]=2)[CH:30]=[CH:29][C:28]=1[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 24758Sodium hydrideHCID 673341233-Amino-N-(4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)quinazolin-6-yl)propanamide

Product 1

HCID 67335525HCID 67335525, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

44 mg of sodium hydride (60%, oil suspension) dissolved in 2 ml of THF was reacted with 0.03 ml of dimethylethanol for 30 mins, 100 mg of the compound obtained (20-1) of Example 20 dissolved in 5 ml of THF was added thereto at 0° C., and the resulting solution was reacted for 3 hours while heating to room temperature. The reacted solution was diluted with saturated sodium bicarbonate solution, extracted with chloroform, dried over anhydrous magnesium sulfate, filtered and distilled under a reduced pressure, and the resulting residue was subjected to column chromatography (eluent-chloroform:methanol=15:1) to obtain the title compound (70 mg, 64%).

Sources & evidence

ORD record
ord-63c32ad1cbdb482695e5342d80f9f7d3
Source dataset
uspto-grants-2011_08
Patent number
US08003658B2

Reaction notes

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