Methyl Acrylate → HCID 54341699, compound

HRID 361456Notes

Reaction equation

HRID 361456 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([S:14]([N:17]([C:27]([O:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[O:28])[C:18]3[C:23]([O:24][CH3:25])=[N:22][C:21]([CH3:26])=[CH:20][N:19]=3)(=[O:16])=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:34]([O:38][CH3:39])(=[O:37])[CH:35]=[CH2:36].C(N(CC)CC)C>CN(C)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:30]([O:29][C:27]([N:17]([C:18]1[C:23]([O:24][CH3:25])=[N:22][C:21]([CH3:26])=[CH:20][N:19]=1)[S:14]([C:13]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH:36]=[CH:35][C:34]([O:38][CH3:39])=[O:37])=[CH:3][CH:4]=2)=[N:9][CH:10]=[CH:11][CH:12]=1)(=[O:16])=[O:15])=[O:28])[CH:31]([CH3:33])[CH3:32]

Participants

7

Reactant 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 211862652-(4-iodophenyl)-N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide

Product 1

HCID 54341699HCID 54341699, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(4-iodophenyl)-N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (1.5 g), methyl acrylate (0.25 ml), palladium acetate (58 mg) and triethylamine (1.79 ml) in dimethyl formamide (45 ml) and water (5 ml) was heated at 100° C. for 1 hour. Volatile material was removed by evaporation and water (50 ml) was added to the residue. The mixture was acidfied to pH 3 with 1M hydrochloric acid and extracted with ethyl acetate (2×50 ml). The extracts were washed with water (50 ml) and saturated sodium chloride solution (50 ml), treated with charcoal and dried (MgSO4). The solvent was removed by evaporation and the residue was triturated with ether/hexane (1:1 v/v) to give N-isobutoxycarbonyl-2-[4-(2-[methoxycarbonyl]vinyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.99 g), m.p. 149°-151° C.; microanalysis found: C, 57.7; H, 5.2; N, 10.6%; C26H28N4O7S requires: C, 57.8; H, 5.2; N, 10.4%.

Workup

  1. customVolatile material was removed by evaporation and water (50 ml)
  2. additionwas added to the residue
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. washThe extracts were washed with water (50 ml) and saturated sodium chloride solution (50 ml)
  5. additiontreated with charcoal
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed by evaporation
  8. customthe residue was triturated with ether/hexane (1:1 v/v)

Sources & evidence

ORD record
ord-bd3230f2db104085afd998f64d28a32a
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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