Trifluoroacetic acid → 6-(Benzoylamino)-4-{[4-chloro-3-(trifluoromethyl)benzyl]amino}quinazoline-8-carboxamide

HRID 578646Notes

Reaction equation

HRID 578646 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.[NH2:17][C:18]1[CH:19]=[C:20]2[C:25](=[C:26]([C:28]([NH2:30])=[O:29])[CH:27]=1)[N:24]=[CH:23][N:22]=[C:21]2[NH:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([C:40]([F:43])([F:42])[F:41])[CH:34]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([NH:17][C:18]1[CH:19]=[C:20]2[C:25](=[C:26]([C:28]([NH2:30])=[O:29])[CH:27]=1)[N:24]=[CH:23][N:22]=[C:21]2[NH:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([C:40]([F:42])([F:43])[F:41])[CH:34]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 667631316-Amino-4-{[4-chloro-3-(trifluoromethyl)benzyl]amino}quinazoline-8-carboxamide

Product 1

HCID 667636056-(Benzoylamino)-4-{[4-chloro-3-(trifluoromethyl)benzyl]amino}quinazoline-8-carboxamideYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (66 μL, 0.5 M in anhydrous DCM, 0.03 mmol, 1.1 equiv.) was added to a solution of TFA salt of 6-amino-4-{[4-chloro-3-(trifluoromethyl)benzyl]amino}quinazoline-8-carboxamide (15 mg, 0.03 mmol, 1.0 equiv.) and triethylamine (16 μL, 0.09 mmol, 3.0 equiv.) in anhydrous DCM (1 mL). The resulting mixture was stirred at rt for 3 h. Purification by pre-HPLC gave the title compound in 83% yield. Mass: M+H+: 500.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-a00581739e3b40fd9d410b940c1001ed
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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