Methanesulfonyl chloride → HCID 22341778, compound

HRID 2249707Notes

Reaction equation

HRID 2249707 reaction equation
[C:1]([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:18])=[C:16]([CH3:17])[N:11]3[CH:10]=[CH:9][C:8]=2[C@@H:7](O)[CH2:6][C@H:5]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:3])[CH3:2].CS(Cl)(=O)=O>ClCCl.C(N(CC)CC)C>[C:1]([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:18])=[C:16]([CH3:17])[N:11]3[CH:10]=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 69291707HCID 69291707, compound

Product 1

HCID 22341778HCID 22341778, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

6.0 g (17.9 mmol) of rel-(7S,9S)-10-acetyl-7-hydroxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine (racemic) are dissolved in 100 ml of dichloromethane and 20 ml of triethylamine. A solution of 2.9 g (25 mmol) of methanesulphonyl chloride in 5 ml of dichloromethane is then added dropwise with ice cooling within 30 min. After 2 h, hydrolysis is effected using water and extraction using dichloromethane. The organic phase is dried over magnesium sulphate and evaporated. The residue is crystallized using diethyl ether. 4.8 g (85%) of the title compound are isolated as a pale brown solid (m.p. 170° C.).

Workup

  1. customhydrolysis
  2. extractionwater and extraction
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. customevaporated
  5. customThe residue is crystallized

Sources & evidence

ORD record
ord-57d5466f55dc426fa581fa72bb105987
Source dataset
uspto-grants-2008_01
Patent number
US07314935B2

Reaction notes

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