Pyridine → HCID 22272502, compound

HRID 346783Notes

Reaction equation

HRID 346783 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:18]1[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20][CH2:19]1.[CH3:32][S:33](Cl)(=[O:35])=[O:34].N1C=CC=CC=1>>[NH:11]([S:8]([C:6]1[CH:5]=[CH:4][C:3]([N:18]2[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20][CH2:19]2)=[C:2]([NH:1][S:33]([CH3:32])(=[O:35])=[O:34])[CH:7]=1)(=[O:9])=[O:10])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 22272440HCID 22272440, compound

Product 1

HCID 22272502HCID 22272502, compoundYield 58%

Procedure

A mixture of tert-butyl 4-[2-amino-4-(anilinosulfonyl)phenyl]-1,4-diazepane-1-carboxylate (176 mg, 0.39 mmol), methylsulfonyl chloride (0.040 mL, 0.47 mmol) and pyridine (0.285 mL, 3.51 mmol) in CH2CL2 (5 mL) was stirred at room temperature overnight. The reaction mixture was quenched with NaHCO3 aq (3×30 mL). The organic phase was separated, dried (MgSO4) and filtered. The volatiles were evaporated followed by purification of the oily residue by chromatography (SiO2, hexane/EtOAc 4:1) to give 110 mg of tert-butyl 4-{4-(anilinosulfonyl)-2-[(methylsulfonyl)amino]phenyl}-1,4-diazepane-1-carboxylate (yield 58%).

Workup

  1. customThe reaction mixture was quenched with NaHCO3 aq (3×30 mL)
  2. customThe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe volatiles were evaporated
  6. customfollowed by purification of the oily residue by chromatography (SiO2, hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-531607002d9a4942a6ba8c8c100107e8
Source dataset
uspto-grants-2007_02
Patent number
US07173035B2

Reaction notes

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