Hydrochloric Acid → N-(5-amino-2-chloropyridin-3-yl)morpholine-4-sulfonamide

HRID 1812418Notes

Reaction equation

HRID 1812418 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][S:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:6][C:5]([N:18]=C(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:4][N:3]=1.Cl>C1COCC1>[NH2:18][C:5]1[CH:6]=[C:7]([NH:8][S:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])[C:2]([Cl:1])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86647078N-(2-chloro-5-(diphenylmethyleneamino)pyridin-3-yl)morpholine-4-sulfonamide

Product 1

HCID 71481004N-(5-amino-2-chloropyridin-3-yl)morpholine-4-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-chloro-5-(diphenylmethyleneamino)pyridin-3-yl)morpholine-4-sulfonamide (0.150 g, 0.328 mmol) in THF (3 mL) was added hydrochloric acid, 2 n (JT Baker) (0.020 mL, 0.657 mmol). The reaction was stirred at rt in closed system for 20 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 (24 g, 3% MeOH in DCM) to afford the desired product as a white foam-like solid (70.0 mg). MS (ESI pos. ion) m/z: 293.0. 1H NMR (300 MHz, CDCl3) δ ppm 3.16-3.32 (m, 4H) 3.61-3.74 (m, 4H) 3.84 (br. s., 2H) 6.67 (br. s., 1H) 7.31 (d, J=2.34 Hz, 1H) 7.64 (d, J=2.19 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 (24 g, 3% MeOH in DCM)

Sources & evidence

ORD record
ord-b263aa0be86b4f6d8c8879fb904baef8
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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