Triethylamine → HCID 87274267, compound

HRID 1869586Notes

Reaction equation

HRID 1869586 reaction equation
[CH:1]1([N:7]2[CH2:12][CH2:11][N:10]([C:13]3[S:17][C:16]([NH:18][C:19](=[O:28])[C:20]4[CH:25]=[CH:24][C:23]([CH:26]=O)=[CH:22][CH:21]=4)=[N:15][C:14]=3[C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([N:38](CC)CC)C.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>C1COCC1>[CH:1]1([N:7]2[CH2:12][CH2:11][N:10]([C:13]3[S:17][C:16]([NH:18][C:19](=[O:28])[C:20]4[CH:21]=[CH:22][C:23]([CH2:26][NH:38][S:44]([CH3:43])(=[O:46])=[O:45])=[CH:24][CH:25]=4)=[N:15][C:14]=3[C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57986740HCID 57986740, compound

Product 1

HCID 87274267HCID 87274267, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.15 g of the compound of Example 149 was suspended in 5 ml of THF, 0.2 ml of triethylamine and a solution of 35 mg of methanesulfonyl chloride in 2 ml of THF were sequentially added thereto under ice cooling, and the mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated, mixed with water, and extracted with EtOAc. The obtained organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the thus-obtained residue was recrystallized from EtOAc-hexane mixed solvent to obtain 0.12 g of N-[5-(4-cyclohexylpiperazin-1-yl)-4-(4-fluorophenyl)thiazol-2-yl]-4-(methanesulfonylaminomethyl)benzamide. The obtained compound was suspended in 5 ml of EtOAc, 0.2 ml of 1M HCl-EtOAc solution was added under ice cooling, and the mixture was stirred overnight. The thus-precipitated solid was filtered and dried to obtain 111 mg of N-[5-(4-cyclohexylpiperazin-1-yl)-4-(4-fluorophenyl)thiazol-2-yl]-4-(methanesulfonylaminomethyl)benzamide hydrochloride.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionmixed with water
  3. extractionextracted with EtOAc
  4. washThe obtained organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. customthe thus-obtained residue was recrystallized from EtOAc-hexane mixed solvent

Sources & evidence

ORD record
ord-9e66579ade6c47e4befc03668f694a82
Source dataset
uspto-grants-2009_12
Patent number
US07638536B2

Reaction notes

Loading…