Potassium Carbonate → [4-(5-Carbamoylpyrazin-2-yloxy)benzyl]phenethylcarbamic acid tert-butyl ester

HRID 228277Notes

Reaction equation

Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([NH2:10])=[O:9])=[N:6][CH:7]=1.[C:11]([O:15][C:16](=[O:34])[N:17]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1)[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:14])([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:11]([O:15][C:16](=[O:34])[N:17]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][C:2]2[CH:7]=[N:6][C:5]([C:8](=[O:9])[NH2:10])=[CH:4][N:3]=2)=[CH:29][CH:28]=1)[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

Conditions

Temperature: 140 °C

Procedure

Take up 5-chloropyrazine-2-carboxamide (0.0527 g, 0.334 mmol), (4-hydroxybenzyl)phenethylcarbamic acid tert-butyl ester (Example 380, Part B) (0.110 g, 0.334 mmol) and K2CO3 (0.116 g, 0.836 mmol) in DMF (0.80 mL). Heat at 140° C. for 21.5 hours. Concentrate the reaction mixture then purify by flash chromatography, eluting with 50% ethyl acetate in hexanes to give the title compound (0.019 g, 12.7%):

Workup

concentrationConcentrate the reaction mixture
customthen purify by flash chromatography
washeluting with 50% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-4789ec0fc21247c4934dd11ac5c7e8a3
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560463B2

Reaction notes

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