Hydrochloric Acid → 3-(5-Amino-6-cyclopropanecarbonyl-pyrazin-2-yl)-N-(2-methoxy-ethyl)-benzenesulfonamide

HRID 81468Notes

Reaction equation

HRID 81468 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.CON(C)[C:9]([C:11]1[C:16]([NH2:17])=[N:15][CH:14]=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([S:24](=[O:31])(=[O:30])[NH:25][CH2:26][CH2:27][O:28][CH3:29])[CH:19]=2)[N:12]=1)=[O:10].Cl>C1COCC1>[NH2:17][C:16]1[N:15]=[CH:14][C:13]([C:18]2[CH:19]=[C:20]([S:24]([NH:25][CH2:26][CH2:27][O:28][CH3:29])(=[O:30])=[O:31])[CH:21]=[CH:22][CH:23]=2)=[N:12][C:11]=1[C:9]([CH:1]1[CH2:2][CH2:3]1)=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 86634546HCID 86634546, compoundHCID 178418630HCID 178418630, compound2×

Product 1

HCID 442363973-(5-Amino-6-cyclopropanecarbonyl-pyrazin-2-yl)-N-(2-methoxy-ethyl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A 1M solution of cyclopropyl magnesium bromide in THF (1.3 ml, 1.3 mmol) is added to a solution of 3-amino-6-[3-(2-methoxy-ethylsulfamoyl)-phenyl]-pyrazine-2-carboxylic acid methoxy-methyl-amide (Intermediate CB) (0.49 g, 1.24 mmol) in anhydrous THF (15 ml) under N2. The orange solution is stirred at room temperature for 18 hours after which time a 1M solution of cyclopropyl magnesium bromide in THF (1.3 ml, 1.3 mmol) is added. The orange solution is stirred at room temperature for 1 hour. 1M HCl (45 ml) is added and the product extracted into EtOAc (120 ml), dried (MgSO4), and concentrated in vacuo. Purification by flash chromatography (SiO2, 50-100% EtOAc in iso-hexane) yields the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-6) δ 9.08 (1H, s), 8.51 (1H, m), 8.39 (1H, d), 8.22-7.90 (2H, br), 7.88 (2H, m), 7.76 (1H, t), 3.73 (1H, m) 3.37 (2H, t), 3.21 (3H, s), 3.02 (2H, q), 1.19 (2H, m), 1.14 (2H, m); MS m/z 377 [M+H]+

Workup

  1. additionis added
  2. extractionthe product extracted into EtOAc (120 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (SiO2, 50-100% EtOAc in iso-hexane)

Sources & evidence

ORD record
ord-d76a843dc1cb4ea4a5d8ec7fe337fbc7
Source dataset
uspto-grants-2014_09
Patent number
US08846687B2

Reaction notes

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