Hydrochloric Acid → HCID 22272483, compound

HRID 230537Notes

Reaction equation

HRID 230537 reaction equation
[NH:1]([S:8]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:23][CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]2)=[C:13]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[CH:12]=1)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOCC.[ClH:41]>CO>[ClH:41].[N:17]1([C:14]2[CH:15]=[CH:16][C:11]([S:8]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)(=[O:10])=[O:9])=[CH:12][C:13]=2[NH:31][S:32]([CH3:35])(=[O:33])=[O:34])[CH2:23][CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 22272502HCID 22272502, compound

Product 1

HCID 22272483HCID 22272483, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl 4-{4-(anilinosulfonyl)-2-[(methylsulfonyl)amino]phenyl}-1,4-diazepane-1-carboxylate (0.077 g, 0.147 mmol) was dissolved in MeOH, and ether saturated with HCl gas was added. The mixture was stirred at room temperature for 4 h and then concentrated. The crude solid was dissolved in a small amount of MeOH, and ether was added. The precipitate was collected and dried to give 30 mg of the pure product as the HCl salt (yield 48%): 1H NMR (DMSO-d6) δ 7.72-7.70 (m, 1H), 7.46-7.42 (m, 1H), 7.25-7.20 (m, 3H), 7.14-7.09 (m, 2H), 7.03-6.99 (m, 1H), 3.45-3.15 (m, partly obscured by solvent signal, HDO, 6H), 2.96 (s, 3H), 2.02-1.95 (m, 2H); MS (posES-FIA) m/z=425 (M+H+).

Workup

  1. concentrationconcentrated
  2. dissolutionThe crude solid was dissolved in a small amount of MeOH, and ether
  3. additionwas added
  4. customThe precipitate was collected
  5. customdried

Sources & evidence

ORD record
ord-7f31f00b4e5c48678a60dbbe8378f571
Source dataset
uspto-grants-2009_07
Patent number
US07566715B2

Reaction notes

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