Tetrahydrofuran → HCID 58612182, compound

HRID 1442648Notes

Reaction equation

HRID 1442648 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Na].C1COCC1.[Cl:16][C:17]1[CH:25]=[CH:24][C:20]2[O:21][CH2:22][O:23][C:19]=2[C:18]=1[NH2:26].Cl[C:28]1[C:33]([C:34]#[N:35])=[CH:32][N:31]=[C:30]2[N:36]=[C:37]([S:39][CH3:40])[S:38][C:29]=12>CN(C=O)C.O>[Cl:16][C:17]1[CH:25]=[CH:24][C:20]2[O:21][CH2:22][O:23][C:19]=2[C:18]=1[NH:26][C:28]1[C:33]([C:34]#[N:35])=[CH:32][N:31]=[C:30]2[N:36]=[C:37]([S:39][CH3:40])[S:38][C:29]=12

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 113672535-Chloro-1,3-benzodioxol-4-amineHCID 11715695HCID 11715695, compoundHCID 45051731Sodium hexamethyidisilazane

Product 1

HCID 58612182HCID 58612182, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

1M sodium hexamethyldisilazane in THF (1.42 mL, 1.42 mmol) was added to 5-chloro-benzo[1,3]dioxol-4-ylamine Compound 31a (as described in PCT Application WO03/008409) (221 mg, 1.29 mmol) in DMF at 0° C. and the mixture was stirred for 15 min. 7-chloro-2-methylsulfanyl-thiazolo[4,5-b]pyridine-6-carbonitrile Compound 1g (312 mg, 1.29 mmol) in DMF (1 mL) was added and the reaction mixture stirred for an additional 2 hr at ambient temperature. The mixture was then diluted with water and filtered through Celite 545 to form a plug. The celite plug was rinsed with EtOAc and the organic layer was isolated and washed with brine. The organic layer was dried over MgSO4, then filtered and evaporated onto silica gel. Isolation by flash chromatography (eluted with a 20 to 40% EtOAc/hexane gradient) gave 7-(5-chloro-benzo[1,3]dioxol-4-ylamino)-2-methylsulfanyl-thiazolo[4,5-b]pyridine-6-carbonitrile Compound 31b (30 mg) as a yellow oil. MS 377, 379 (MH+).

Workup

  1. stirringthe reaction mixture stirred for an additional 2 hr at ambient temperature
  2. filtrationfiltered through Celite 545
  3. customto form a plug
  4. washThe celite plug was rinsed with EtOAc
  5. customthe organic layer was isolated
  6. washwashed with brine
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated onto silica gel
  10. washIsolation by flash chromatography (eluted with a 20 to 40% EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-634197276f31452195170d54943c988a
Source dataset
uspto-grants-2010_02
Patent number
US07659284B2

Reaction notes

Loading…