HCID 118222069, compound → HCID 118222067, compound

HRID 713164Notes

Reaction equation

HRID 713164 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-4e1c5b82a2984af6a72d6aee93be6996
Source dataset
uspto-grants-2015_11
Patent number
US09181288B2

Reaction notes

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