HCID 118222069, compound → HCID 118222067, compound

HRID 523644Notes

Reaction equation

HRID 523644 reaction equation
C([O:8][CH:9]1[CH2:15][CH2:14][CH2:13][N:12]([S:16]([C:19]2[CH:20]=[C:21]([CH:33]=[CH:34][C:35]=2[CH2:36][CH2:37][F:38])[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[C:27]([Cl:32])[CH:26]=2)=[O:23])(=[O:18])=[O:17])[CH2:11][CH2:10]1)C1C=CC=CC=1>CO.[Pd]>[Cl:32][C:27]1[CH:26]=[C:25]([NH:24][C:22](=[O:23])[C:21]2[CH:33]=[CH:34][C:35]([CH2:36][CH2:37][F:38])=[C:19]([S:16]([N:12]3[CH2:13][CH2:14][CH2:15][CH:9]([OH:8])[CH2:10][CH2:11]3)(=[O:18])=[O:17])[CH:20]=2)[CH:30]=[CH:29][C:28]=1[F:31]

Participants

4

Reactant 1

HCID 118222069HCID 118222069, compound

Product 1

HCID 118222067HCID 118222067, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-(4-benzyloxyazepan-1-yl)sulfonyl-N-(3-chloro-4-fluoro-phenyl)-4-(2-fluoroethyl)benzamide (65.00 mg, 115.44 umol, 1.00 Eq) in MeOH (15 mL) was added Pd/C (30.00 mg, 115.44 umol, 1.00 Eq) under N2. The suspension was degassed under vacuum and purged with H2 several times. The mixture was stirred under H2 at 25° C. for 16 hr. TLC showed the starting material was consumed completely. The reaction mixture was filtered and the filter was concentrated, purified by prep-TLC (eluting with PE:EA=1:1) to afford product N-(3-chloro-4-fluoro-phenyl)-4-(2-fluoroethyl)-3-(4-hydroxyazepan-1-yl)sulfonyl-benzamide (24.00 mg, 50.75 umol, 43.96% yield) as white solid.

Workup

  1. customThe suspension was degassed under vacuum
  2. custompurged with H2 several times
  3. customwas consumed completely
  4. filtrationThe reaction mixture was filtered
  5. concentrationthe filter was concentrated
  6. custompurified by prep-TLC (eluting with PE:EA=1:1)

Sources & evidence

ORD record
ord-7a66997c8af64d3fb213d58ca7ac0bcc
Source dataset
uspto-grants-2016_05
Patent number
US09339510B2

Reaction notes

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