HCID 19973458, compound → HCID 19973432, compound

HRID 1452038Notes

Reaction equation

HRID 1452038 reaction equation
CC(C)([O-])C.[K+].Cl[CH2:8][CH2:9][CH2:10][CH2:11][S:12]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]2[N:19]([CH:21]=[CH:22][N:23]=2)[CH:20]=1)=[O:13]>O1CCCC1.CN(C)P(=O)(N(C)C)N(C)C>[N:23]1[CH:22]=[CH:21][N:19]2[CH:20]=[C:15]([CH:14]3[CH2:8][CH2:9][CH2:10][CH2:11][S:12]3=[O:13])[CH:16]=[CH:17][C:18]=12

Participants

4

Reactant 2

HCID 19973458HCID 19973458, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19973432HCID 19973432, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 86583969tetrahydrofuran HMPASolvent2×

Procedure

8.68 g of potassium t-butoxide was added to 80 ml of a tetrahydrofuran/hexamethylphosphoric triamide [4:1 (v/v)] mixture, followed by the cooling with ice. A solution of 9.51 g of the 6-((4-chlorobutyl)sulfinylmethyl)imidazo[1,2-a]pyridine prepared in the Preparative Example 8 in 30 ml of a tetrahydrofuran/hexamethylphosphoric triamide [4:1 (v/v)] mixture was dropped into the obtained mixture. The obtained mixture was stirred for one hour. Followed by the addition of ice-water. The obtained mixture was extracted with chloroform. The organic phase was dried over anhydrous magnesium sulfate and distilled to remove the solvent. The obtained oil was solidified by allowing to stand, followed by the addition of ether. The obtained mixture was filtered to give 5.84 g of the title compound as a dark-creamy powder (yield: 71%). The NMR spectroscopic analysis of this powder revealed that the powder was a mixture comprising two diastereomers at a ratio of about 2:1

Workup

  1. additionwas dropped into the obtained mixture
  2. extractionThe obtained mixture was extracted with chloroform
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. distillationdistilled
  5. customto remove the solvent
  6. additionfollowed by the addition of ether
  7. filtrationThe obtained mixture was filtered

Sources & evidence

ORD record
ord-a41ade9efcc247df9f37108ec48347f9
Source dataset
uspto-grants-1997_02
Patent number
US05606061

Reaction notes

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