Methanesulfonyl chloride → HCID 9844801, compound

HRID 1267935Notes

Reaction equation

HRID 1267935 reaction equation
CS(Cl)(=O)=O.[F:6][C:7]1[CH:8]=[C:9]([NH:14][CH2:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25]O)[C:20]=2[CH3:27])=[O:17])[CH:10]=[CH:11][C:12]=1[F:13].C(N(CC)C(C)C)(C)C.[C:37]([N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)(=[O:39])[CH3:38]>O1CCCC1>[C:37]([N:40]1[CH2:45][CH2:44][N:43]([CH2:25][C:21]2[C:20]([CH3:27])=[C:19]([NH:18][C:16](=[O:17])[CH2:15][NH:14][C:9]3[CH:10]=[CH:11][C:12]([F:13])=[C:7]([F:6])[CH:8]=3)[CH:24]=[CH:23][CH:22]=2)[CH2:42][CH2:41]1)(=[O:39])[CH3:38]

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 837951-AcetylpiperazineHCID 18542414HCID 18542414, compound

Product 1

HCID 9844801HCID 9844801, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methane sulphonyl chloride (0.06ml) was added to a solution of the product of step (d) (0.12 g) and N,N-diisopropylethylamine (0.28 ml) in tetrahydrofuran (3ml). The reaction mixture was stirred at room temperature for 1.5 hours. A solution of 1-acetylpiperazine (0. 15 g) in tetrahydrofuran (1 ml) was added and the mixture was heated at reflux for 2 hours. The reaction mixture was partitioned between ethyl acetate and water and the organic phase was washed with water and brine, dried (MgSO4) and evaporated. The crude product was triturated with ethyl acetate/isohexane to give the product as a pale yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. washthe organic phase was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was triturated with ethyl acetate/isohexane

Sources & evidence

ORD record
ord-cd54efeb1fa44b539297372f8dc93845
Source dataset
uspto-grants-2003_04
Patent number
US06555541B1

Reaction notes

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