Acetic Acid → HCID 10128112, compound

HRID 1444016Notes

Reaction equation

HRID 1444016 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=O)[CH:22]=2)=[N:17][C:16]([Cl:29])=[CH:15][N:14]=1)(=[O:11])=[O:10].CN.C(O)(=O)C.[C:36]([BH3-])#[N:37].[Na+]>O1CCCC1.CO.O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][NH:37][CH3:36])[CH:22]=2)=[N:17][C:16]([Cl:29])=[CH:15][N:14]=1)(=[O:11])=[O:10]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 59168126HCID 59168126, compound

Product 1

HCID 10128112HCID 10128112, compoundYield 33.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,3-dichloro-N-[5-chloro-3-(3-formylphenylmethoxy)-2-pyrazinyl]benzenesulphonamide (Example 107a) (0.1 g), methylamine (2 mL of a 2M solution in tetrahydrofuran) and acetic acid (0.2 mL) in methanol (2 mL) was stirred at room temperature. After 2 h, sodium cyanoborohydride (0.03 g) was added. After 0.5 h, water (2 mL) was added and the mixture evaporated to dryness. Chromatography on silica gel eluting with methanol/dichloromethane mixtures gave the title compound as a white solid (0.035 g).

Workup

  1. waitAfter 0.5 h
  2. customthe mixture evaporated to dryness

Sources & evidence

ORD record
ord-3ee13325fe124476bc7bd14bbedf77fd
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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