Trifluoroacetic acid → HCID 44441995, compound

HRID 2080264Notes

Reaction equation

HRID 2080264 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:12]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].C(N(CC)C(C)C)(C)C.FC(F)(F)C(O)=O>CN1CCCC1=O>[C:12]([C:16]1[CH:17]=[CH:18][C:19]([CH2:20][NH:21][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][N:3]=2)=[CH:22][CH:23]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 788644-ChloroquinazolineHCID 81531DiisopropylethylamineHCID 27356554-tert-Butylbenzylamine

Product 1

HCID 44441995HCID 44441995, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 4-chloro-quinazoline described in Preparation Example X-1 (8 mg, 0.049 mmol) in 1-methyl-2-pyrrolidone (0.5 mL) were added 4-tert-butyl-benzylamine (10 μl, 0.059 mmol) and N,N-diisopropylethylamine (17 μl, 0.098 mmol), and the solution was stirred for 5 hours at 160° C. The reaction mixture was directly purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and the title compound (16.5 mg, 0.041 mmol, 72%) was obtained as a trifluoroacetic acid salt.

Workup

  1. customThe reaction mixture was directly purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used)

Sources & evidence

ORD record
ord-72599048e6974a958451b0a6d3e1007e
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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