Acetone → HCID 67102055, compound

HRID 2079654Notes

Reaction equation

HRID 2079654 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[N:13][C:14]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=4)=[N:15]3)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[CH3:29][C:30]([CH3:32])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH:30]([N:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[N:13][C:14]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=4)=[N:15]3)=[CH:10][CH:9]=2)[CH2:3][CH2:2]1)([CH3:32])[CH3:29]

Participants

6

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 67102123HCID 67102123, compound

Product 1

HCID 67102055HCID 67102055, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To 7-(piperidin-4-yloxy)-N-(3-(trifluoromethyl)phenyl)quinazolin-2-amine in DCM was added acetone (10 eq), a few drops of acetic acid and sodium triacetoxy borohydride (4 eq). The reaction mixture was stirred for 16 h at ambient temperature. The reductive amination went to completion to give 7-(1-isopropylpiperidin-4-yloxy)-N-(3-(trifluoromethyl)phenyl)quinazolin-2-amine. The mixture was then purified on prep HPLC to give 7-(1-isopropylpiperidin-4-yloxy)-N-(3-(trifluoromethyl)phenyl)quinazolin-2-amine. ES/MS m/z 431 (MH+).

Sources & evidence

ORD record
ord-414392627bd243d2a52b83bfafad73f2
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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