Triethylamine → HCID 44227502, compound

HRID 2068639Notes

Reaction equation

HRID 2068639 reaction equation
[N:1]1([C:8]([C:10]2[CH:14]=[C:13]([C:15]3[CH:16]=[N:17][NH:18][CH:19]=3)[S:12][CH:11]=2)=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl>[CH3:27][S:28]([N:4]1[CH2:5][CH2:6][CH2:7][N:1]([C:8]([C:10]2[CH:14]=[C:13]([C:15]3[CH:16]=[N:17][NH:18][CH:19]=3)[S:12][CH:11]=2)=[O:9])[CH2:2][CH2:3]1)(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 44227503HCID 44227503, compound

Product 1

HCID 44227502HCID 44227502, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[1,4]Diazepan-1-yl-[5-(1H-pyrazol-4-yl)-thiophen-3-yl]-methanone (0.075 g, 0.27 mmol) was dissolved in DCM (30 mL) and cooled in an ice-bath before addition of triethylamine (0.082 g, 0.82 mmol) and methanesulfonyl chloride (0.038 g, 0.33 mmol). The reaction mixture was stirred at room temperature for 2 hours. The solvent was removed by evaporation and the residue taken up in methanol (2.5 mL) and treated with sodium hydroxide (1 M, 0.3 mL). After 1 hour the solvent was removed and the crude material was purified by HPLC, eluting with 5%-98% acetonitrile in water (0.1% formic acid) over 20 minutes. The fractions containing the desired product were combined and freeze-dried to give the title compound (0.045 g). LCMS m/z 355.14 [M+H]+ R.T.=5.95 min (Analytical Method 2).

Workup

  1. customThe solvent was removed by evaporation
  2. additiontreated with sodium hydroxide (1 M, 0.3 mL)
  3. customAfter 1 hour the solvent was removed
  4. customthe crude material was purified by HPLC
  5. washeluting with 5%-98% acetonitrile in water (0.1% formic acid) over 20 minutes
  6. additionThe fractions containing the desired product
  7. customfreeze-dried

Sources & evidence

ORD record
ord-b1848d64675642748ee2e7d55862493f
Source dataset
uspto-grants-2012_10
Patent number
US08299063B2

Reaction notes

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