HCID 86719970, compound → HCID 86719971, compound

HRID 1617331Notes

Reaction equation

HRID 1617331 reaction equation
[CH3:1][O:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([C:15]3[NH:19][N:18]=[CH:17][CH:16]=3)=[CH2:14])=[CH:12][C:7]=2[S:6][C:5]1=[O:20]>CCOC(C)=O.[Pd]>[CH3:1][O:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]([C:15]3[NH:19][N:18]=[CH:17][CH:16]=3)[CH3:14])=[CH:12][C:7]=2[S:6][C:5]1=[O:20]

Participants

4

Reactant 1

HCID 86719970HCID 86719970, compound

Product 1

HCID 86719971HCID 86719971, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

Add 5% palladium/carbon (15 g; 7.0 mmoles) to a N2 purged flask and add EtOAc (250 mL). Add 3-(methoxymethyl)-6-[1-(1H-pyrazol-5-yl)ethenyl]-3H-1,3-benzothiazol-2-one (29 g, 101 mmoles) as a solution in EtOAc (250 mL). Degas under vacuum and charge with hydrogen via balloon. Stir overnight, evacuate excess hydrogen under pressure and flush with N2. Filter through diatomaceous earth and concentrate to give 3-(methoxymethyl)-6-[1-(1H-pyrazol-5-yl)ethyl]-3H-1,3-benzothiazol-2-one as a thick yellow oil (27 g, 93 mmoles; 92% yield). Material may be carried into the next step without further purification. LCMS (Low) rt=1.73 min., M+1=290.

Workup

  1. customDegas under vacuum
  2. additioncharge with hydrogen via balloon
  3. customevacuate excess hydrogen under pressure
  4. customflush with N2
  5. filtrationFilter through diatomaceous earth
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-43c4bbc595314bfab8f9235ced78f01f
Source dataset
uspto-grants-2014_07
Patent number
US08765960B2

Reaction notes

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