HCID 58458939, compound → HCID 136163958, compound

HRID 390356Notes

Reaction equation

HRID 390356 reaction equation
C([O:8][C:9]1[C:10](=[O:34])[N:11]([CH3:33])[C:12]([CH:28]2[CH2:32][CH2:31][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>[CH:28]1([C:12]2[N:11]([CH3:33])[C:10](=[O:34])[C:9]([OH:8])=[C:14]([C:15]3[O:19][N:18]=[C:17]([CH2:20][C:21]4[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=4)[N:16]=3)[N:13]=2)[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

3

Reactant 1

HCID 58458939HCID 58458939, compound

Product 1

HCID 136163958HCID 136163958, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5-(benzyloxy)-2-cyclopentyl-6-(3-(4-fluorobenzyl)-1,2,4-oxadiazol-5-yl)-3-methylpyrimidin-4(3H)-one (0.248 g, 0.54 mmol) in TFA (5 mL) was stirred 4 h at room temperature. The resulting yellow reaction mixture was then concentrated and the residue was crystallized from EtOH/H2O to afford the title (0.184 g, 92% yield) as a yellow solid. 1HNMR (500 MHz, CDCl3) δ: 9.74 (1H, s), 7.30 (2H, dd, J=8.2, 5.5 Hz), 7.01 (2H, t, J=8.6 Hz), 4.15 (2H, s), 3.64 (3H, s), 3.21-3.15 (1H, m), 2.04-2.00 (4H, m), 1.89-1.82 (2H, m), 1.72-1.64 (2H, m). HRMS (M+H) calcd for C19H20N4O3F: 371.1520. found: 371.1535. Anal calcd for C19H19N4O3F: C, 61.61; H, 5.17; N, 15.12; F, 5.13. found: C, 61.92; H, 5.54; N, 14.87; F, 5.10.

Workup

  1. concentrationThe resulting yellow reaction mixture was then concentrated
  2. customthe residue was crystallized from EtOH/H2O
  3. customto afford the title (0.184 g, 92% yield) as a yellow solid

Sources & evidence

ORD record
ord-d3236b3fc6c64c129bdfc0f1aa630922
Source dataset
uspto-grants-2013_02
Patent number
US08383639B2

Reaction notes

Loading…