Triethylamine → 3-{4-[(dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 20543Notes

Reaction equation

HRID 20543 reaction equation
Cl[C:2]1[CH:29]=[C:28]([S:30]([N:33]([CH3:35])[CH3:34])(=[O:32])=[O:31])[CH:27]=[CH:26][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:17]=[C:18]([O:20][C@@H:21]([CH3:25])[CH2:22][O:23][CH3:24])[CH:19]=1)[C:8]([NH:10][C:11]1[CH:15]=[CH:14][N:13]([CH3:16])[N:12]=1)=[O:9].C(N(CC)CC)C>CO.C1COCC1.[Pd]>[CH3:35][N:33]([CH3:34])[S:30]([C:28]1[CH:29]=[CH:2][C:3]([O:4][C:5]2[CH:6]=[C:7]([CH:17]=[C:18]([O:20][C@@H:21]([CH3:25])[CH2:22][O:23][CH3:24])[CH:19]=2)[C:8]([NH:10][C:11]2[CH:15]=[CH:14][N:13]([CH3:16])[N:12]=2)=[O:9])=[CH:26][CH:27]=1)(=[O:31])=[O:32]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 115409373-{2-chloro-4-[(dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

Product 1

HCID 115983163-{4-[(dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamideYield 32.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{2-chloro-4-[(dimethylamino)sulfonyl]phenoxy}-5-[(1S)-2-methoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide (1.0 g, 1.9 mmol) in methanol (20 mL) and THF (20 mL) was added triethylamine (1.5 mL) and 10% palladium on carbon (100 mg). The resulting mixture was stirred under an atmosphere of hydrogen for 20 hours. The mixture was filtered through Celite® and evaporated under reduced pressure. The residue was dissolved in DCM (100 mL) and washed with 2M hydrochloric acid (100 mL). The organic phase was separated and the aqueous reextracted with DCM (100 mL). The combined organic extracts were dried (MgSO4) and evaporated to afford the title compound (300 mg, 32%).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. customevaporated under reduced pressure
  3. dissolutionThe residue was dissolved in DCM (100 mL)
  4. washwashed with 2M hydrochloric acid (100 mL)
  5. customThe organic phase was separated
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-dae1c8dce7914aeda10e9030581e2bb0
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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