HCID 68784936, compound → 4-(5-Cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-{[1-(2-isopropylpyrimidin-4-yl)piperidin-4-yl]methyl}benzamide

HRID 2093591Notes

Reaction equation

HRID 2093591 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:37]([CH3:39])[CH3:38])[C:6]2[O:10][C:9]([C:11]3[CH:35]=[CH:34][C:14]([C:15]([NH:17][CH2:18][CH:19]4[CH2:24][CH2:23][N:22]([C:25]5[CH:30]=[CH:29][N:28]=[C:27]([C:31]([CH3:33])=[CH2:32])[N:26]=5)[CH2:21][CH2:20]4)=[O:16])=[CH:13][CH:12]=3)=[N:8][C:7]=2[CH:36]=1)#[N:2]>CO.O1CCCC1.[Pd]>[C:1]([C:3]1[CH:4]=[C:5]([CH:37]([CH3:39])[CH3:38])[C:6]2[O:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([C:15]([NH:17][CH2:18][CH:19]4[CH2:24][CH2:23][N:22]([C:25]5[CH:30]=[CH:29][N:28]=[C:27]([CH:31]([CH3:32])[CH3:33])[N:26]=5)[CH2:21][CH2:20]4)=[O:16])=[CH:34][CH:35]=3)=[N:8][C:7]=2[CH:36]=1)#[N:2]

Participants

5

Reactant 1

HCID 68784936HCID 68784936, compound

Product 1

HCID 251702104-(5-Cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-{[1-(2-isopropylpyrimidin-4-yl)piperidin-4-yl]methyl}benzamideYield 1,115.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(5-cyano-7-isopropyl-1,3-benzoxazol-2-yl)-N-{[1-(2-isopropenylpyrimidin-4-yl)piperidin-4-yl]methyl}benzamide (10 mg) in 1.33 ml of methanol and 0.66 ml of tetrahydrofuran was added 3 mg of 10% palladium on carbon. This mixture was evacuated and flushed with a hydrogen-filled balloon ten times. The reaction mixture was stirred at 50° C. for 1 h, and then at room temperature for 15 h. The mixture was then filtered through a plug of Celite, eluting with methanol. After concentration of the eluent in vacuo, the residue was further purified by filtration through a plug of silica gel, eluting with ethyl acetate. Concentration of the residue in vacuo provided the title compound (112 mg, 93%). Mass spectrum (ESI) 523.4 (M+1). 1H NMR (500 MHz, CDCl3): δ 8.34 (d, J=8.3 Hz, 2H), 8.16 (d, J=6.2 Hz, 1H), 7.95 (d, J=8.0 Hz, 3H), 7.52 (s, 1H), 6.32 (m, 3H), 4.52 (d, J=9.1 Hz, 2H), 3.46 (m, 3H), 2.97 (sept, J=6.9 Hz, 1H), 2.91 (t, J=11.3 Hz, 2H), 2.00 (s, 1H), 1.88 (d, J=12.1 Hz, 2H), 1.46 (d, J=6.8, 6H), 1.33 (m, 2H), 1.28 (d, J=6.9, 6H).

Workup

  1. customThis mixture was evacuated
  2. customflushed with a hydrogen-
  3. additionfilled balloon ten times
  4. waitat room temperature for 15 h
  5. filtrationThe mixture was then filtered through a plug of Celite
  6. washeluting with methanol
  7. filtrationAfter concentration of the eluent in vacuo, the residue was further purified by filtration through a plug of silica gel
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-a58cf680c0dd48749e15efed057f7fce
Source dataset
uspto-grants-2013_05
Patent number
US08445480B2

Reaction notes

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