Ethanol → 2-Cyclopropyl-7-[2-(dimethylamino)ethyl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17607Notes

Reaction equation

HRID 17607 reaction equation
C(O)C.[C:4]([C:6]1[C:11]2[N:12]=[C:13]([CH:15]3[CH2:17][CH2:16]3)[O:14][C:10]=2[C:9]([CH2:18][C:19](=S)[N:20]([CH3:22])[CH3:21])=[C:8]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:7]=1[CH3:30])#[N:5]>[Ni].O1CCCC1>[CH:15]1([C:13]2[O:14][C:10]3[C:11](=[C:6]([C:4]#[N:5])[C:7]([CH3:30])=[C:8]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:9]=3[CH2:18][CH2:19][N:20]([CH3:21])[CH3:22])[N:12]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 2

HCID 702EthanolHCID 866308822-(4-Cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)-N,N-dimethylethanethioamide

Product 1

HCID 685859192-Cyclopropyl-7-[2-(dimethylamino)ethyl]-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 47%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Raney nickel (corresponding to 0.2 ml) was added to an ethanol (1 ml)/tetrahydrofuran (1 ml) solution of 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)-N,N-dimethylethanethioamide (I-314) (14.0 mg, 0.037 mmol), followed by stirring in an oil bath at 50° C. for 5 hours. The reaction liquid was filtered, the filtrate was concentrated, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=10:1, v/v) to obtain the entitled compound (6.00 mg, 47%) as a white solid.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated
  4. customthe resulting residue was purified by preparative TLC (eluent, chloroform

Sources & evidence

ORD record
ord-52b3350bcc5c486388cb12429730f8aa
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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