Hydrochloric Acid → {3-Amino-6-[2-methyl-5-(morpholine-4-sulfonyl)-phenyl]-pyrazin-2-yl}-cyclopropyl-methanone

HRID 2387192Notes

Reaction equation

HRID 2387192 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]=[C:22]([S:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)(=[O:26])=[O:25])[CH:21]=[CH:20][C:19]=2[CH3:33])[N:12]=1)=[O:10].Cl>C1COCC1>[NH2:17][C:16]1[C:11]([C:9]([CH:1]2[CH2:3][CH2:2]2)=[O:10])=[N:12][C:13]([C:18]2[CH:23]=[C:22]([S:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)(=[O:26])=[O:25])[CH:21]=[CH:20][C:19]=2[CH3:33])=[CH:14][N:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 866345433-Amino-6-[2-methyl-5-(morpholine-4-sulfonyl)-phenyl]-pyrazine-2-carboxylic acid methoxy-methyl amide2×HCID 178418630HCID 178418630, compound2×

Product 1

HCID 44233343{3-Amino-6-[2-methyl-5-(morpholine-4-sulfonyl)-phenyl]-pyrazin-2-yl}-cyclopropyl-methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A 1M solution of cyclopropyl magnesium bromide in THF (0.21 ml, 0.21 mmol) is added to a solution of 3-amino-6-[2-methyl-5-(morpholine-4-sulfonyl)-phenyl]-pyrazine-2-carboxylic acid methoxy-methyl amide (Intermediate C) (0.058 mg, 0.14 mmol) in anhydrous THF (3 ml) under N2. The orange solution is stirred at room temperature for 2 hours after which time a 1M solution of cyclopropyl magnesium bromide in THF (0.21 ml, 0.21 mmol) is added. The orange solution is stirred at room temperature for 1 hour. 1M HCl (15 ml) is added, and the product extracted into EtOAc (30 ml), dried (MgSO4), and concentrated in vacuo. Purification by flash chromatography (SiO2, 33-50% EtOAc in iso-hexane) yields the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.63 (1H, s), 7.92 (2H, bs), 7.79 (1H, s), 7.70-7.63 (2H, m), 3.64-3.62 (4H, m), 3.49-3.43 (1H, m), 2.90 (4H, bs) 2.54 (3H, s), 1.09-1.01 (4H, m); MS m/z 403 [M+H]+

Workup

  1. additionis added
  2. extractionthe product extracted into EtOAc (30 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (SiO2, 33-50% EtOAc in iso-hexane)

Sources & evidence

ORD record
ord-c55ff6b2456d475ab8dd346009eafe7d
Source dataset
uspto-grants-2012_09
Patent number
US08268834B2

Reaction notes

Loading…