HCID 66621105, compound → HCID 66621049, compound

HRID 415149Notes

Reaction equation

HRID 415149 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[O:15][C:16]2[C:22]([C:23]([NH2:25])=[O:24])=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1.[H][H]>CO.O=[Pt]=O>[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][NH:9]2)[CH:5]=[CH:4][C:3]=1[C:14]1[O:15][C:16]2[C:22]([C:23]([NH2:25])=[O:24])=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1

Participants

5

Reactant 2

HCID 66621105HCID 66621105, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66621049HCID 66621049, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

2-(2-Fluoro-4-(pyridin-2-yl)phenyl)benzo[d]oxazole-7-carboxamide (380 mg, 1.1 mmol) and PtO2 (190 mg) in methanol (20 ml) was hydrogenated under 25 atm of hydrogen at 45° C. for two days. The mixture was filtered. The solvent was removed in vacuum. The crude product was purified by prep-HPLC to give 2-(2-fluoro-4-(piperidin-2-yl)phenyl)benzo[d]oxazole-7-carboxamide (228 mg, yield 44%). 1H-NMR (400 MHz, CD3OD) δ (ppm): 1.76-1.90 (m, 2H), 1.96-2.06 (m, 3H), 2.13-2.16 (m, 1H), 3.19-3.25 (m, 1H), 3.52-3.55 (d, J=12.4 Hz, 1H); 4.37-4.40 (d, J=11.2 Hz, 1H); 7.27-7.40 (m, 1H); 7.49-7.53 (m, 3H); 7.92-7.93 (m, 2H); 8.35-8.39 (t, J=7.2 Hz, 3H); LC-MS (ESI) m/z: 340 (M+1)+.

Workup

  1. filtrationThe mixture was filtered
  2. customThe solvent was removed in vacuum
  3. customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record
ord-c1bfe92fd7804747816c3eac1b7d8626
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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