Dimethylformamide → HCID 59467884, compound

HRID 1404945Notes

Reaction equation

HRID 1404945 reaction equation
[S:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[C:2]1[SH:10].CN(C=O)C.[H-].[Na+].Cl[CH2:19][C:20]([N:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][CH2:23]1)=[O:21]>C1COCC1.CCOC(C)=O.O.C(Cl)Cl.CCOC(C)=O>[N:22]1([C:20](=[O:21])[CH2:19][S:10][C:2]2[S:1][C:9]3[CH:8]=[CH:7][N:6]=[CH:5][C:4]=3[N:3]=2)[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][CH2:23]1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 2401372-Chloro-1-(1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-oneHCID 178527814Thiazolo[4,5-c]pyridine-2-thiol

Product 1

HCID 59467884HCID 59467884, compoundYield 49%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

Compound 68 (0.5 g, 3.0 mmol) was mixed with 20 mL of dry THF and 20 mL of dry DMF under N2 and the suspension was stirred for 30 min at RT and then cooled to 0° C. NaH (0.15 g 60% in mineral oil, 3.7 mmol) was added to the ice-cold suspension which became a greenish solution upon stirring for several minutes at 0° C. The reaction mixture was stirred for another 30 min at 0° C. and then 2-chloro-1-(3,4-dihydroquinolin-1(2H)-yl)ethanone (0.63 g, 3.0 mmol) dissolved in 5 ml of dry THF was added. After the reaction mixture was stirred for 16 h at RT (monitored by TLC (CH2Cl2/EtOAc=1:1 and MS), it was diluted with 100 mL of EtOAc followed by addition of 50 mL of H2O. The organic layer was separated and the aqueous layer was extracted with EtOAc (2×50 mL). The organic layers were combined washed with water, brine, dried over Na2SO4 and concentrated giving 1.1 g of crude which was purified by flash chromatography (CH2Cl2/EtOAc) to yield compound 69 (0.5 g, 49%). MS: m/z+ 342.1 [M+H]+; Anal. Calcd (found) for C17H15N3OS2: C, 59.80 (59.89); H, 4.43 (4.51); N, 12.31 (12.12); S, 18.78 (18.53).

Workup

  1. temperaturecooled to 0° C
  2. stirringupon stirring for several minutes at 0° C
  3. stirringThe reaction mixture was stirred for another 30 min at 0° C.
  4. additionwas added
  5. stirringAfter the reaction mixture was stirred for 16 h at RT (
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with EtOAc (2×50 mL)
  8. washThe organic layers were combined washed with water, brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated
  11. customgiving 1.1 g of crude which
  12. customwas purified by flash chromatography (CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-0ea41366f76940a6be8e285d0c43ad37
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

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