Dichloromethane → HCID 54341699, compound

HRID 1107494Notes

Reaction equation

HRID 1107494 reaction equation
[CH2:1]([O:5][C:6]([N:8]([C:26]1[C:31]([O:32][CH3:33])=[N:30][C:29]([CH3:34])=[CH:28][N:27]=1)[S:9]([C:12]1[C:13]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]=O)=[CH:20][CH:19]=2)=[N:14][CH:15]=[CH:16][CH:17]=1)(=[O:11])=[O:10])=[O:7])[CH:2]([CH3:4])[CH3:3].[Br-].[C:36]([CH2:39][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:38])=[O:37].[OH-].[Na+].[CH2:61](Cl)Cl>O>[CH2:1]([O:5][C:6]([N:8]([C:26]1[C:31]([O:32][CH3:33])=[N:30][C:29]([CH3:34])=[CH:28][N:27]=1)[S:9]([C:12]1[C:13]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[CH:39][C:36]([O:38][CH3:61])=[O:37])=[CH:20][CH:19]=2)=[N:14][CH:15]=[CH:16][CH:17]=1)(=[O:10])=[O:11])=[O:7])[CH:2]([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 21186316N-isobutoxycarbonyl-2-(4-formylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamideHCID 21186329Carboxymethyl triphenylphosphonium bromide

Product 1

HCID 54341699HCID 54341699, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-isobutoxycarbonyl-2-(4-formylphenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (500 mg) was added to carboxymethyl triphenylphosphonium bromide (429 mg) in a mixture of saturated aqueous sodium hydroxide (1.25 ml) and methylene chloride (4 ml) and stirred vigorously at ambient temperature for 1.5 hours. Water (20 ml) was added and the mixture extracted with dichloromethane (2×20 ml). The combined organic extracts were, washed with water (5 ml), dried (MgSO4) and evaporated. The residue was purified by chromatography on a Mega Bond Elut column, eluting with a gradient of 0-30% ethyl acetate in hexane. Fractions containing the product were combined, evaporated and the residue was triturated with diethyl ether/isohexane (1:1 v/v) and filtered to give N-isobutoxycarbonyl-2-[4-(2-[methoxycarbonyl]vinyl)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (366 mg), m.p 155-156° C.; 1H NMR (CDCl3): 0.65 (d, 6H), 1.7 (septet, 1H), 2.5 (s, 3H), 3.82 (s, 3H), 3.85 (d, 2H), 3.98 (s, 3H), 6.48 (d, 1H), 7.4-7.8 (m, 7H), 7.9 (s, 1H), 8.86 (dd, 1H), 8.98 (dd, 1H).

Workup

  1. extractionthe mixture extracted with dichloromethane (2×20 ml)
  2. washwashed with water (5 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by chromatography on a Mega Bond Elut column
  6. washeluting with a gradient of 0-30% ethyl acetate in hexane
  7. additionFractions containing the product
  8. customevaporated
  9. customthe residue was triturated with diethyl ether/isohexane (1:1 v/v)
  10. filtrationfiltered

Sources & evidence

ORD record
ord-1c589938eead48659923a641abd09d74
Source dataset
uspto-grants-2000_05
Patent number
US06060475

Reaction notes

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