p-Toluenesulfonic acid monohydrate → 2-[(Benzyloxy)methyl]-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17347Notes

Reaction equation

HRID 17347 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([NH:12][C:13]1[C:18](O)=[C:17]([F:20])[C:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:15]([CH3:27])[C:14]=1[C:28]#[N:29])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH2:1]([O:8][CH2:9][C:10]1[O:11][C:18]2[C:13](=[C:14]([C:28]#[N:29])[C:15]([CH3:27])=[C:16]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:17]=2[F:20])[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 866308382-(benzyloxy)-N-(5-cyano-2-fluoro-3-hydroxy-6-methylbiphenyl-4-yl)acetamide

Product 1

HCID 685869132-[(Benzyloxy)methyl]-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Procedure

Similarly, 2-(benzyloxy)-N-(3-cyano-6-fluoro-5-hydroxy-2-methyl[1,1′-biphenyl]-4-yl)acetamide (I-89) (418 mg, 1.07 mmol) was dissolve din toluene (8.4 ml), p-toluenesulfonic acid monohydrate (84 mg, 20 wt. %) was added, followed by heating under reflux for 18 hours.

Workup

  1. additionwas added
  2. temperatureby heating
  3. temperatureunder reflux for 18 hours

Sources & evidence

ORD record
ord-ffb179ff20e1473398f8d446b62d2b58
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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