Trifluoroacetic acid → 7-(piperazin-1-yl)-3,4-dihydroquinazolin-2(1H)-one

HRID 1520115Notes

Reaction equation

HRID 1520115 reaction equation
[O:1]=[C:2]1[NH:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([N:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)=[CH:7][CH:8]=2)[NH:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl.C1COCC1>[N:12]1([C:6]2[CH:5]=[C:4]3[C:9]([CH2:10][NH:11][C:2](=[O:1])[NH:3]3)=[CH:8][CH:7]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117796384tert-Butyl 4-(2-oxo-1,2,3,4-tetrahydroquinazolin-7-yl)piperazine-1-carboxylate

Product 1

HCID 1177594787-(piperazin-1-yl)-3,4-dihydroquinazolin-2(1H)-oneYield 134.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 16 (0.7 g, 2.11 mmol) in a mixture of CH2Cl2 (15 mL) and THF (5 mL) at 0° C. was added TFA (5 mL) and the mixture was stirred at room temperature for 6 h. The solvent was evaporated under vacuum to afford 0.66 g (96%) of compound 5 as a dark brown gum. IR (KBr) νmax. cm−1: 3261 (NH), 3032 (Ar—H), 1691 (C═O), 1613, 1513, 1415 (C═C). 1H NMR (500 MHz, DMSO-d6) δ=3.18 (m, 4H, 2CH2); 3.42 (m, 4H, 2CH2); 4.23 (s, 2H, CH2); 6.66 (m, 2H, aromatic-H); 6.73 (m, 1H, aromatic-H); 8.80 (br. s, 1H, NH); 8.86 (br. s, 1H, NH); 13C NMR (125.7 MHz, DMSO-d6) δ=46.35 (CH2), 46.73 (CH2), 48.63 (CH2), 114.19 (aromatic-C), 114.38 (aromatic-C), 116.49 (aromatic-C), 118.83 (aromatic-C), 131.87 (aromatic-C), 144.81 (aromatic-C), 154.72 (C═O). Calculated (%) for C14H16F3N4O2 (329.12); C: 48.56, H: 4.95, N: 16.18. found (%); C: 48.45, H: 5.05, N: 16.15.

Workup

  1. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-19485fa299c64523a96ce5009d7341f8
Source dataset
uspto-grants-2015_07
Patent number
US09073900B2

Reaction notes

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