4-Toluenesulfonyl chloride → HCID 22063579, compound

HRID 1828479Notes

Reaction equation

HRID 1828479 reaction equation
O[C:2]1[N:3]=[C:4]2[CH:12]=[C:11]([CH2:13][CH2:14][C:15]3[S:16][CH:17]=[C:18]([CH:20]([CH3:22])[CH3:21])[N:19]=3)[CH:10]=[CH:9][N:5]2[C:6](=[O:8])[CH:7]=1.C(N(CC)CC)C.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[NH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1>C(Cl)Cl>[CH:20]([C:18]1[N:19]=[C:15]([CH2:14][CH2:13][C:11]2[CH:10]=[CH:9][N:5]3[C:6](=[O:8])[CH:7]=[C:2]([N:41]4[CH2:46][CH2:45][O:44][CH2:43][CH2:42]4)[N:3]=[C:4]3[CH:12]=2)[S:16][CH:17]=1)([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8083MorpholineHCID 8471TriethylamineHCID 135749047HCID 135749047, compound2×

Product 1

HCID 22063579HCID 22063579, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 2-hydroxy-8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4 H-pyrido[1,2-a]-pyrimidin-4-one (500 mg) obtained in (A) was dissolved in methylene chloride (20 ml), added with triethylamine (0.26 ml) and p-toluenesulfonyl chloride (360 mg) and stirred for 24 hours under nitrogen atmosphere. The reaction solution was added with morpholine (0.83 ml) and stirred for 12 hours, and the solvent was evaporated. The residue was purified by silica gel column chromatography to obtain the title compound (273 mg).

Workup

  1. stirringstirred for 12 hours
  2. customthe solvent was evaporated
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-621de2717764449ca017391d4323bb17
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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