HCID 19973458, compound → HCID 19389855, compound

HRID 1757109Notes

Reaction equation

HRID 1757109 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>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)[CH:16]=[CH:17][C:18]=12

Participants

4

Reactant 2

HCID 19973458HCID 19973458, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19389855HCID 19389855, compoundYield 76.2%

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-ca6267e79b9a400e8e2f9ec70d82474a
Source dataset
uspto-grants-1995_08
Patent number
US05444066

Reaction notes

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