HCID 58458920, compound → HCID 136224431, compound

HRID 390359Notes

Reaction equation

HRID 390359 reaction equation
C([O:8][C:9]1[C:18](=[O:19])[N:17]2[C:12]([C:13]([CH3:21])([CH3:20])[O:14][CH2:15][CH2:16]2)=[N:11][C:10]=1[C:22]1[O:23][C:24]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[N:25][N:26]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[F:34][C:31]1[CH:32]=[CH:33][C:28]([CH2:27][C:24]2[O:23][C:22]([C:10]3[N:11]=[C:12]4[N:17]([C:18](=[O:19])[C:9]=3[OH:8])[CH2:16][CH2:15][O:14][C:13]4([CH3:21])[CH3:20])=[N:26][N:25]=2)=[CH:29][CH:30]=1

Participants

3

Reactant 1

HCID 58458920HCID 58458920, compound

Product 1

HCID 136224431HCID 136224431, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-(benzyloxy)-2-(5-(4-fluorobenzyl)-1,3,4-oxadiazol-2-yl)-9,9-dimethyl-6,7-dihydropyrimido[2,1-c][1,4]oxazin-4(9H)-one (0.071 g, 0.15 mmol) in TFA (5 mL) was stirred 22 h at room temperature. The reaction mixture was then concentrated and purified by preparative HPLC on a C18 column using water/MeOH containing 0.1% TFA as eluent to afford the title compound (0.035 g, 60% yield) as white solid. 1HNMR (500 MHz, CDCl3) δ: 9.71 (1H, s), 7.35 (2H, dd, J=8.6, 5.5 Hz), 7.06 (2H, t, J=8.6 Hz), 4.30 (2H, s), 4.07-4.03 (4H, m), 1.63 (6H, s). HRMS (M+H) calcd for C18H18N4O4F: 373.1312. found: 373.1326. Anal calcd for C18H17N4O4F: C, 58.06; H, 4.60; N, 15.04. found: C, 57.88; H, 4.72; N, 14.87.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. custompurified by preparative HPLC on a C18 column

Sources & evidence

ORD record
ord-f45876bbb62a4ebe94f40ecf6fc1e0de
Source dataset
uspto-grants-2013_02
Patent number
US08383639B2

Reaction notes

Loading…