HCID 59205098, compound → HCID 59205104, compound

HRID 2241926Notes

Reaction equation

HRID 2241926 reaction equation
[F:1][CH:2]([F:32])[O:3][CH2:4][C@@H:5]([O:7][C:8]1[CH:9]=[C:10]([CH:21]=[C:22]([O:24]CC2C=CC=CC=2)[CH:23]=1)[C:11]([NH:13][C:14]1[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=1)=[O:12])[CH3:6]>C(O)C>[F:32][CH:2]([F:1])[O:3][CH2:4][C@@H:5]([O:7][C:8]1[CH:9]=[C:10]([CH:21]=[C:22]([OH:24])[CH:23]=1)[C:11]([NH:13][C:14]1[CH:19]=[N:18][C:17]([CH3:20])=[CH:16][N:15]=1)=[O:12])[CH3:6]

Participants

3

Reactant 1

HCID 59205098HCID 59205098, compound

Product 1

HCID 59205104HCID 59205104, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-[(2S)-1-(difluoromethoxy)propan-2-yl]oxy-N-(5-methylpyrazin-2-yl)-5-phenylmethoxy-benzamide (0.48 g, 1.08 mmol) was dissolved in ethanol (10 mL) and THF (10 mL) and the flask evacuated and purged with argon (3 times). 10% Palladium on carbon (48 mg) was added and the flask further evacuated and finally purged with hydrogen gas. The reaction mixture was stirred at RT for 20 hours. The reaction mixture was evacuated and purged with argon (3 times) and the catalyst removed by filtration through Celite®. The filtrate was concentrated in vacuo to give the desired compound (0.38 g).

Workup

  1. customTHF (10 mL) and the flask evacuated
  2. custompurged with argon (3 times)
  3. addition10% Palladium on carbon (48 mg) was added
  4. customthe flask further evacuated
  5. customfinally purged with hydrogen gas
  6. customThe reaction mixture was evacuated
  7. custompurged with argon (3 times)
  8. customthe catalyst removed by filtration through Celite®
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c33ceeb55f7a42928cf33a32bc32120c
Source dataset
uspto-grants-2010_03
Patent number
US07671060B2

Reaction notes

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