Trifluoroacetic acid → N2-(3-(Dimethylamino)propyl)-N4-(piperidin-4-yl)quinazoline-2,4-diamine

HRID 215921Notes

Reaction equation

HRID 215921 reaction equation
[CH3:1][N:2]([CH3:31])[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[N:16]=[C:15]([NH:17][CH:18]2[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]2)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1.C(O)(C(F)(F)F)=O.N.CO>C(Cl)Cl>[CH3:31][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[N:16]=[C:15]([NH:17][CH:18]2[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]2)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21705897Ammonia methanolHCID 58006221tert-Butyl 4-(2-(3-(Dimethylamino)propylamino)quinazolin-4-ylamino)piperidine-1-carboxylate

Product 1

HCID 58006203N2-(3-(Dimethylamino)propyl)-N4-(piperidin-4-yl)quinazoline-2,4-diamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(2-(3-(dimethylamino)propylamino)quinazolin-4-ylamino)piperidine-1-carboxylate (3.3 g, 7.71 mmol) in CH2Cl2 (20 ml) at 0° C. was added CF3COOH (4 ml, 53.9 mmol) and the reaction was stirred at room temperature overnight. The reaction mixture was then neutralized with 7 N NH3-MeOH. The resulting white solid was filtered away. The filtrate was concentrated and purified by silica gel column chromatography using 10% NH3 ca. 7 N MeOH in CH2Cl2 and 90% CH2Cl2 solution as eluent to obtain the title compound as a pure white solid.

Workup

  1. filtrationThe resulting white solid was filtered away
  2. concentrationThe filtrate was concentrated
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-c5cbabfea4e24e89a6b722e196ea7361
Source dataset
uspto-grants-2012_06
Patent number
US08193203B2

Reaction notes

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