4-[1-(6,7-Dimethoxyquinazolin-2-yl)piperidin-4-ylamino]benzoic acid tert-butyl ester → 4-[1-(6,7-Dimethoxyquinazolin-2-yl)piperidin-4-ylamino]benzoic acid

HRID 1274140Notes

Reaction equation

HRID 1274140 reaction equation
C([O:5][C:6](=[O:34])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[N:29]=[CH:28][C:27]4[C:22](=[CH:23][C:24]([O:32][CH3:33])=[C:25]([O:30][CH3:31])[CH:26]=4)[N:21]=3)[CH2:16][CH2:15]2)=[CH:9][CH:8]=1)(C)(C)C>FC(F)(F)C(O)=O>[CH3:31][O:30][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][C:24]=1[O:32][CH3:33])[N:21]=[C:20]([N:17]1[CH2:16][CH2:15][CH:14]([NH:13][C:10]3[CH:9]=[CH:8][C:7]([C:6]([OH:34])=[O:5])=[CH:12][CH:11]=3)[CH2:19][CH2:18]1)[N:29]=[CH:28]2

Participants

3

Reactant 1

HCID 98256994-[1-(6,7-Dimethoxyquinazolin-2-yl)piperidin-4-ylamino]benzoic acid tert-butyl ester

Product 1

HCID 99532664-[1-(6,7-Dimethoxyquinazolin-2-yl)piperidin-4-ylamino]benzoic acidYield 168.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (13) (0.014 g, 0.029 mmol) in trifluoroacetic acid (3 mL) was capped with a drying tube and stirred at 25° C. for 12 h. The reaction mixture was evaporated to a yellow solid residue (0.020 g, quantitative yield); 1H NMR (DMSO) δ 8.95 (s, 1H), 7.66 (d, 2H, J=8.7), 7.23 (s, 1H), 6.94 (s, 1H), 6.62 (d, 2H, J=8.8), 4.67 (d, 2H, J=13.6), 3.90 (s, 3H), 3.83 (s, 3H), 3.64 (m, 1H), 3.19 (t, 2H, J=11.5), 2.00 (d, 2H, J=12.8), 1.38 (m, 2H); 13C NMR (DMSO) δ 167.5, 157.9, 156.3, 151.6, 146.6, 131.2, 129.6, 123.9, 116.7, 113.8, 111.2, 105.6, 104.0, 55.9, 55.6, 48.8, 42.7, 31.2; HRMS (FAB) m/z 409.1878 (M+H)+ (C22H24N4O4 requires 409.1876); Anal. (C22H24N4O4 ·3CF3COOH·11/4H2O·1CH3OH) C, H, N.

Sources & evidence

ORD record
ord-965f15f2bf8e4e19b8609272eedc777d
Source dataset
uspto-grants-2000_12
Patent number
US06156758

Reaction notes

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