Acetic Acid → HCID 21186273, compound

HRID 361439Notes

Reaction equation

HRID 361439 reaction equation
[NH2:1][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)(=O)[CH3:35].[C:38]([BH3-])#N.[Na+].Cl>CC(C)=O.O>[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]([NH:1][CH:34]([CH3:35])[CH3:38])=[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 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 21186303HCID 21186303, compound

Product 1

HCID 21186273HCID 21186273, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 2-(4-aminophenyl)-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.17 g) in acetone (3 ml) and water (3 ml) was acidified to pH 4 with glacial acetic acid. Sodium cyanotrihydridoborate (0.045 g) was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was then poured into 2M hydrochloric acid (10 ml) and extracted with ethyl acetate (2×25 ml). The aqueous layer was basified to pH 10 with 2M sodium hydroxide and re-extracted with ethyl acetate (2×25 ml). All of the organic extracts were combined, washed with brine and dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by gradient elution with 35-50% ethyl acetate/hexane through a silica gel Mega Bond Elut column to give N-isobutoxycarbonyl-N-(3-methoxy-5-methylpyrazin-2-yl)-2-[4-(isopropylamino)phenyl]pyridine-3-sulphonamide (0.11 g) as a gum; 1H NMR (d6 -DMSO): 0.6 (d, 6 H), 1.2 (d, 6 H), 1.6 (m, 1 H), 3.6 (m, 1 H), 3.8 (d, 2 H), 4.0 (s, 3 H), 5.8 (d, 1 H), 6.6 (d, 2 H), 7.35 (d, 2 H), 7.6 (m, 1 H), 8.2 (s, 1 H), 8.8 (m, 2 H); mass spectrum (+ve ESP): 514 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (2×25 ml)
  2. extractionre-extracted with ethyl acetate (2×25 ml)
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customVolatile material was removed by evaporation
  6. customthe residue was purified by gradient elution with 35-50% ethyl acetate/hexane through a silica gel Mega Bond Elut column

Sources & evidence

ORD record
ord-0df376280d8d4c21bc9e2a61dcc2b6dc
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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