Hydrochloric Acid → N-(5-amino-2-methylpyridin-3-yl)methanesulfonamide

HRID 1622020Notes

Reaction equation

HRID 1622020 reaction equation
C1(C(=[N:14][C:15]2[CH:16]=[C:17]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[C:18]([CH3:21])=[N:19][CH:20]=2)C2C=CC=CC=2)C=CC=CC=1.Cl>C1COCC1>[NH2:14][C:15]1[CH:16]=[C:17]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[C:18]([CH3:21])=[N:19][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86647089N-(5-(Diphenylmethyleneamino)-2-methylpyridin-3-YL)methanesulfonamide

Product 1

HCID 66600561N-(5-amino-2-methylpyridin-3-yl)methanesulfonamideYield 29.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(5-(diphenylmethyleneamino)-2-methylpyridin-3-yl)methanesulfonamide (0.430 g, 1.177 mmol) in THF (10 mL) was added hydrochloric acid (JT Baker) (1.765 mL, 1.765 mmol) (1N). The reaction was stirred at rt in closed system for min. The reaction mixture was partitioned between EtOAc and sat. NaHCO3. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layer were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (40 g, 5% to 10% MeOH in DCM) to afford the desired product as a brown solid (70.0 mg). MS (ESI pos. ion) m/z: 202.1. 1H NMR (300 MHz, CDCl3) δ ppm 2.42 (s, 3H) 3.03 (s, 3H) 3.70 (br. s., 2H) 6.15 (br. s., 1H) 7.20 (d, J=2.34 Hz, 1H) 7.87 (d, J=2.34 Hz, 1H).

Workup

  1. customThe reaction mixture was partitioned between EtOAc and sat. NaHCO3
  2. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  3. dry with materialThe combined organic layer were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (40 g, 5% to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-a9a1a1f2c05f4c8fb0533d9c7a3048e6
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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