Hydrochloric Acid → HCID 11167116, compound

HRID 914722Notes

Reaction equation

HRID 914722 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]2[S:10][C:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:22])=[O:15])=[CH:12][N:13]=2)[CH2:3][CH2:2]1.Cl.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[S:29](Cl)(=[O:31])=[O:30].CCN(CC)CC>C(Cl)Cl.CO>[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[S:29]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9]2[S:10][C:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:22])=[O:15])=[CH:12][N:13]=2)[CH2:3][CH2:2]1)(=[O:31])=[O:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 58957978HCID 58957978, compound

Product 1

HCID 11167116HCID 11167116, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 35.2 mg (0.1 mmol) {2-[(piperidin-4-ylmethyl)-amino]-thiazol-5-yl}-o-tolyl-methanone; hydrochloride, 21.9 mg (0.12 mmol) thiophene-2-sulfonyl chloride (commercially available) and 44.6 ul (0.32 mmol) NEt3 in a mixture of DCM/MeOH 3/1 was stirred at 60° C. for 16 h. After cooling to room temperature the mixture was concentrated and MeOH (1 ml) and formic acid (0.5 ml) was added and the mixture was subjected to reversed phase HPLC purification eluting with a gradient of acetonitrile/water. After evaporation of the product fractions 22 mg (48%) of the title compound was obtained.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. concentrationwas concentrated
  3. additionMeOH (1 ml) and formic acid (0.5 ml) was added
  4. customthe mixture was subjected to reversed phase HPLC purification
  5. washeluting with a gradient of acetonitrile/water
  6. customAfter evaporation of the product fractions 22 mg (48%) of the title compound
  7. customwas obtained

Sources & evidence

ORD record
ord-46d74d72fc4f40e2b41a4b9911da9c10
Source dataset
uspto-grants-2007_09
Patent number
US07265109B2

Reaction notes

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