Water → HCID 89701557, compound

HRID 1774945Notes

Reaction equation

HRID 1774945 reaction equation
Br[CH:2]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=O.[NH2:29][C:30]1[N:31]=[CH:32][C:33]([C:38]([O:40][CH3:41])=[O:39])=[N:34][C:35]=1[O:36][CH3:37].O>C(O)C.ClCCl>[C:18]([O:17][C:16]([NH:15][C:11]1([C:8]2[CH:9]=[CH:10][C:5]([C:3]3[N:29]=[C:30]4[C:35]([O:36][CH3:37])=[N:34][C:33]([C:38]([O:40][CH3:41])=[O:39])=[CH:32][N:31]4[C:2]=3[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:6][CH:7]=2)[CH2:14][CH2:13][CH2:12]1)=[O:22])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 3

HCID 962WaterHCID 86691038tert-Butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)carbamateHCID 89689648HCID 89689648, compound

Product 1

HCID 89701557HCID 89701557, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of crude tert-butyl (1-{4-[bromo(phenyl)acetyl]phenyl}cyclobutyl)carbamate [Int-1-A] (715 mg, 1.45 mmol, 1.0 eq), methyl 5-amino-6-methoxypyrazine-2-carboxylate (265 mg, 1.45 mmol, 1 eq.; see step 1) were dissolved in ethanol. The reaction vessel was equipped with a Dean-Stark trap containing 4 Å molsieves and then the reaction mixture refluxed for 17 h. The reaction mixture was diluted with 20 mL dichloromethane and treated with water. The organic phase was washed with 1 N hydrochloric acid and brine, filtered through a Whatman-filter and the solvent was removed by the use of a rotary evaporator. Finally purification was achieved via MPLC (Isolera, 50 g Snap-cartridge, eluent:hexane→hexane/ethyl acetate 9/1) to deliver 97 mg (12%).

Workup

  1. customThe reaction vessel was equipped with a Dean-Stark trap
  2. additioncontaining 4 Å molsieves
  3. temperaturethe reaction mixture refluxed for 17 h
  4. washThe organic phase was washed with 1 N hydrochloric acid and brine
  5. filtrationfiltered through
  6. filtrationa Whatman-filter
  7. customthe solvent was removed by the use of a rotary evaporator
  8. customFinally purification

Sources & evidence

ORD record
ord-3a83c0fd452540e0ba96cc0f7df5b095
Source dataset
uspto-grants-2016_02
Patent number
US09260435B2

Reaction notes

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