Hydrochloric Acid → HCID 70103910, compound

HRID 1954060Notes

Reaction equation

HRID 1954060 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH:18]=[CH:17][CH:16]=[CH:15][CH2:14][N:13]2[C:19]([OH:21])=[O:20])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:29][N:30]1[CH:34]=[C:33]([S:35](Cl)(=[O:37])=[O:36])[N:32]=[CH:31]1.Cl>O.O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH:18]=[CH:17][C:16]([S:35]([C:33]3[N:32]=[CH:31][N:30]([CH3:29])[CH:34]=3)(=[O:37])=[O:36])=[CH:15][CH2:14][N:13]2[C:19]([OH:21])=[O:20])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 22457584HCID 22457584, compound

Product 1

HCID 70103910HCID 70103910, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

The 1-[(4-methoxyphenyl)sulfonyl]-diazepine-2-carboxylic acid (0.150 g, 0.48 mmol) is dissolved in water (10 mL) and p-dioxane (10 mL). The triethyl amine (0.27 mL, 1.9 mmol) and 1-methyl-1H-imidazole-4-sulfonyl chloride (0.104 g, 0.58 mmol) are next added. The reaction mixture is stirred overnight at room temperature and then the solution is acidified with 1N HCl to pH~1, poured into water, and extracted with methylene chloride. The organic extracts are dried (Na2SO4) and concentrated down to an oil. The oil is purified by HPLC with a reverse phase column using 70% (95% water, 5% acetonitrile, 0.1% formic acid) and 30% (80% acetonitrile, 20% water) as the eluent.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe organic extracts are dried (Na2SO4)
  3. concentrationconcentrated down to an oil
  4. customThe oil is purified by HPLC with a reverse phase column

Sources & evidence

ORD record
ord-8031c3d4cd9c4c95bcf0c67389930ccc
Source dataset
uspto-grants-2000_09
Patent number
US06121258

Reaction notes

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