HCID 58458927, compound → HCID 136163964, compound

HRID 390355Notes

Reaction equation

HRID 390355 reaction equation
C([O:8][C:9]1[C:10](=[O:35])[N:11]([CH3:34])[C:12]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[N:13][C:14]=1[C:15]1[O:19][N:18]=[C:17]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[N:16]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][C:17]2[N:16]=[C:15]([C:14]3[N:13]=[C:12]([N:28]4[CH2:29][CH2:30][O:31][CH2:32][CH2:33]4)[N:11]([CH3:34])[C:10](=[O:35])[C:9]=3[OH:8])[O:19][N:18]=2)=[CH:22][CH:23]=1

Participants

3

Reactant 1

HCID 58458927HCID 58458927, compound

Product 1

HCID 136163964HCID 136163964, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A yellow solution of 5-(benzyloxy)-6-(3-(4-fluorobenzyl)-1,2,4-oxadiazol-5-yl)-3-methyl-2-morpholinopyrimidin-4(3H)-one (0.216 g, 0.45 mmol) in TFA (10 mL) was stirred 8 h at room temperature. The reaction mixture was then concentrated and the resulting yellow oil was dissolved in MeOH and concentrated to give pale yellow slurry which was triturated with water and filtered to afford the title compound (0.141 g, 80% yield) as a pale off-white solid. 1HNMR (500 MHz, CDCl3) δ: 9.62 (1H, s), 7.30 (2H, dd, J=8.4, 5.4 Hz), 7.01 (2H, t, J=8.6 Hz), 4.15 (2H, s), 3.85-3.83 (4H, m), 3.58 (3H, s), 3.19-3.17 (4H, m). HRMS (M+H) calcd for C18H19N5O4F: 388.1421. found: 388.2924. Anal calcd for C18H18N5O4F: C, 55.81; H, 4.68; N, 18.08; F, 4.90. found: C, 56.16; H, 4.96; N, 17.40; F, 4.94.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. dissolutionthe resulting yellow oil was dissolved in MeOH
  3. concentrationconcentrated
  4. customto give pale yellow slurry which
  5. customwas triturated with water
  6. filtrationfiltered

Sources & evidence

ORD record
ord-d3045655b0614af1bb5ebba440c59dc9
Source dataset
uspto-grants-2013_02
Patent number
US08383639B2

Reaction notes

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