Potassium Carbonate → tert-Butyl N-[(1S,2S)-2-{[3-methyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]carbamate

HRID 1750499Notes

Reaction equation

HRID 1750499 reaction equation
Br[C:2]1[C:3]([NH:12][C@H:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=1.[CH3:26]B(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:26][C:2]1[C:3]([NH:12][C@H:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 118308064tert-butyl ((1S,2S)-2-((3-bromo-5-(trifluoromethyl)pyrazin-2-yl)amino)cyclopentyl)carbamate

Product 1

HCID 118308261tert-Butyl N-[(1S,2S)-2-{[3-methyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]carbamate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl N-[(1S,2S)-2-{[3-bromo-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]carbamate (800 mg, 1.88 mmol), methylboronic acid (CAS number 13061-96-6; 338 mg, 5.64 mmol), tetrakis(triphenylphosphine)palladium (217 mg, 0.19 mmol) and, 2 M potassium carbonate (aq, 3.8 ml, 7.53 mmol) in 1,4-dioxane (6.3 ml) was sealed, evacuated and purged with nitrogen and then subjected to microwave irradiation at 120° C. for 2 hours. The reaction mixture was then diluted with ethyl acetate (40 ml) and water (10 ml). The organics were washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The residue was then purified by column chromatography (silica, 0-50% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customwas sealed
  2. customevacuated
  3. custompurged with nitrogen
  4. customirradiation at 120° C. for 2 hours
  5. additionThe reaction mixture was then diluted with ethyl acetate (40 ml) and water (10 ml)
  6. washThe organics were washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was then purified by column chromatography (silica, 0-50% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-b179aeec026e434a8559fa63346440a1
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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