D-Psicose → HCID 71257317, compound

HRID 710174Notes

Reaction equation

HRID 710174 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[O:13][C:14]2[CH:20]=[C:19]([C:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH:22]=3)[CH:18]=[CH:17][C:15]=2[N:16]=1.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>CO.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[C:12]1[O:13][C:14]2[CH:20]=[C:19]([CH:21]3[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:25][CH2:26]3)[CH:18]=[CH:17][C:15]=2[N:16]=1

Participants

5

Reactant 2

HCID 441036D-PsicoseHCID 71257546HCID 71257546, compound

Product 1

HCID 71257317HCID 71257317, compoundYield 34.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Following the general procedure-1 Tert-butyl 4-{2-[2-fluoro-4-(methylsulfonyl)phenyl]benzo[d]oxazol-6-yl}-5,6-dihydropyridine-1(2H)-carboxylate (35 mg) obtained from intermediate 41 (400 mg, 0.96 mmol) and tert-butyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (318 mg, 0.961 mmol). Tert-butyl 4-{2-[2-fluoro-4-(methylsulfonyl)phenyl]benzo[d]oxazol-6-yl}-5,6-dihydropyridine-1(2H)-carboxylate (50 mg, 0.11 mmol) dissolved in MeOH and added Pd/C (30 mg). This mixture was stirred in an auto clave under hydrogen atmosphere at 55 Psi for 12 h. Reaction mixture filtered through celite and washed the cetile with MeOH. Methanol was removed on rotavapour to obtain the crude. Crude was purified by combiflash using EtOAc and Petether (38:62) as eluent to obtain titled compound (18 mg) as an off-white solid. M.P.: 166.2-169.3° C. 1H-NMR (δ ppm, CDCl3, 400 MHz): 8.48-8.46 (m, 1H), 7.91-7.83 (m, 2H), 7.78 (d, J 8.3, 1H), 7.49 (s, 1H), 7.33-7.25 (m, 1H), 4.35-4.20 (m, 2H), 3.13 (s, 3H), 2.90-2.75 (m, 3H), 1.95-1.85 (m, 2H), 1.75-1.60 (m, 2H), 1.49 (s, 9H).

Workup

  1. customReaction mixture
  2. filtrationfiltered through celite
  3. washwashed the cetile with MeOH
  4. customMethanol was removed on rotavapour
  5. customto obtain the crude
  6. customCrude was purified by combiflash

Sources & evidence

ORD record
ord-806338cd20974d05b0f89fa549439418
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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