HCID 58458930, compound → HCID 136169154, compound

HRID 390358Notes

Reaction equation

HRID 390358 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[S:23][C:24]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[CH: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[S: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][CH:25]=2)=[CH:29][CH:30]=1

Participants

3

Reactant 1

HCID 58458930HCID 58458930, compound

Product 1

HCID 136169154HCID 136169154, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-(benzyloxy)-2-(5-(4-fluorobenzyl)thiazol-2-yl)-9,9-dimethyl-6,7-dihydropyrimido[2,1-c][1,4]oxazin-4(9H)-one (0.051 g, 0.11 mmol) in TFA (5 mL) was stirred 24 h at 40 C. Then, the reaction mixture was cooled, concentrated and purified by preparative HPLC on C18 column using water/MeOH containing 0.1% TFA as eluent to afford the title compound (0.033 g, 80% yield) as pale yellow solid. 1HNMR (500 MHz, CDCl3) δ: 11.51 (1H, s), 7.61 (1H, s), 7.22 (2H, dd, J=8.6, 5.5 Hz), 7.03 (2H, t, J=8.6 Hz), 4.17 (2H, s), 4.06-4.01 (4H, m), 1.60 (6H, s). HRMS (M+H) calcd for C19H19N3O3FS: 388.1131. found: 388.1118. Anal calcd for C19H18N3O3FS: C, 58.90; H, 4.68; N, 10.84. found: C, 58.87; H, 4.47; N, 10.87.

Workup

  1. temperatureThen, the reaction mixture was cooled
  2. concentrationconcentrated
  3. custompurified by preparative HPLC on C18 column

Sources & evidence

ORD record
ord-d93df72004854458ba44ee3920dbf63a
Source dataset
uspto-grants-2013_02
Patent number
US08383639B2

Reaction notes

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