Trifluoroacetic acid → HCID 15947351, compound

HRID 550774Notes

Reaction equation

HRID 550774 reaction equation
Cl.[NH2:2][C:3]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:20])[CH:9]=2)[N:4]=1.C([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]Br)(OC(C)(C)C)=O.C(=O)([O-])[O-].[K+].[K+].C(O)(C(F)(F)F)=O>ClCCl.CCCCCCC.CN(C=O)C>[NH2:2][C:3]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][NH2:28])[CH:14]=2)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:20])[CH:9]=2)[N:4]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 44553605-(BOC-amino)-1-pentyl bromideHCID 67194973HCID 67194973, compound

Product 1

HCID 15947351HCID 15947351, compoundYield 58.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

A mixture of 100 mg of 2-amino-6-chloro-4-(3-hydroxyphenyl)quinazoline hydrochloride, 90.69 mg of 5-(BOC-amino)-1-pentyl bromide, 100 mg of potassium carbonate and 1 ml of DMF is stirred at 40° for 16 hours. The mixture is dissolved in 2 ml of dichloromethane, 1 ml of TFA is added, and the mixture is stirred at room temperature for 4 hours. 3 ml of n-heptane are added, the solvents are removed in vacuo, and the residue is chromatographed, giving 67.9 mg (58.6%) of 2-amino-6-chloro-4-[3-(5-aminopentyloxy)phenyl]quinazoline (“A141”), MW 357.86.

Workup

  1. stirringthe mixture is stirred at room temperature for 4 hours
  2. customthe solvents are removed in vacuo
  3. customthe residue is chromatographed

Sources & evidence

ORD record
ord-836ab213356d4344832f811eae7761e0
Source dataset
uspto-grants-2011_05
Patent number
US07947696B2

Reaction notes

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