Dimethylformamide → HCID 67051249, compound

HRID 2388877Notes

Reaction equation

HRID 2388877 reaction equation
[H-].[Na+].Cl.[N:4]1[CH:9]=[CH:8][C:7]([CH:10]([SH:12])C)=[CH:6][CH:5]=1.[CH3:13][O:14][C:15]1[N:20]=[C:19](SCCC2C=CC=CC=2)[N:18]=[C:17]([NH:30][S:31]([N:34]2[CH2:37][CH2:36][CH2:35]2)(=[O:33])=[O:32])[CH:16]=1.[CH3:38][C:39]([O-])([CH3:41])[CH3:40].[K+].Br.N1C=C[C:48](CBr)=[CH:47][CH:46]=1.CN([CH:56]=[O:57])C>CCOC(C)=O>[CH3:56][O:57][C:47]1[CH:48]=[CH:40][C:39]([CH2:41][N:30]([C:17]2[CH:16]=[C:15]([O:14][CH3:13])[N:20]=[C:19]([S:12][CH2:10][C:7]3[CH:6]=[CH:5][N:4]=[CH:9][CH:8]=3)[N:18]=2)[S:31]([N:34]2[CH2:35][CH2:36][CH2:37]2)(=[O:32])=[O:33])=[CH:38][CH:46]=1

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 127522194-(Bromomethyl)pyridine hbrHCID 23665647Potassium tert-butoxide3×HCID 53628408HCID 53628408, compoundHCID 59558821HCID 59558821, compound

Product 1

HCID 67051249HCID 67051249, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

60% NaH (27 mg) was added batchwise to a solution of 4-pyridylethanethiol hydrochloride (60 mg) in anhydrous DMF (2 ml) stirred under nitrogen. After 30 min. the subtitle product of Example 121 step (0.2 g) was added. The reaction mixture was stirred for a further 18 h. KOtBu (40 mg) was added and after 30 min. a further quantity of KOtBu (40 mg) was added. After 10 min, KOtBu (40 mg) followed by 4-pyridylmethyl bromide hydrobromide (96 mg) were added. The reaction mixture was stirred for 5 min., diluted with EtOAc and washed with H2O and aqueous Na2CO3. The separated organic solution was dried (MgSO4), filtered and the solvent evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel using EtOAc/iso-hexane (7:3) as eluent to give the product as a yellow gum. Yield: 46 mg.

Workup

  1. stirringThe reaction mixture was stirred for a further 18 h
  2. additionwas added
  3. additionwere added
  4. stirringThe reaction mixture was stirred for 5 min.
  5. washwashed with H2O and aqueous Na2CO3
  6. dry with materialThe separated organic solution was dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure
  9. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-ef8d5302b23049cbae2a4b0441074bd5
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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