Water → 4-(5-Amino-6-(5-phenyl-1,2,4-oxadiazol-3-yl)pyrazin-2-yl)benzoic acid

HRID 2204821Notes

Reaction equation

HRID 2204821 reaction equation
Br[C:2]1[N:3]=[C:4]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:11][N:10]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.[C:20]([O-:23])([O-])=[O:21].[Na+].[Na+].O>CC#N.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>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:23])=[O:21])=[CH:16][CH:15]=2)=[N:3][C:4]=1[C:9]1[N:13]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:11][N:10]=1

Participants

6

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 594722055-Bromo-3-(5-phenyl-1,2,4-oxadiazol-3-yl)pyrazin-2-ylamine

Product 1

HCID 594723844-(5-Amino-6-(5-phenyl-1,2,4-oxadiazol-3-yl)pyrazin-2-yl)benzoic acidYield 76%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

5-bromo-3-(5-phenyl-1,2,4-oxadiazol-3-yl)pyrazin-2-amine (200 mg, 0.6287 mmol) 4-carboxyphenylboronic acid (104.3 mg, 0.6287 mmol) and Na2CO3 (133.2 mg, 1.257 mmol) were suspended in MeCN (3.314 mL)/water (3.314 mL) and the mixture de-gassed (×5) and treated with Pd(PPh3)4 (72.65 mg, 0.06287 mmol). The reaction was de-gassed again and heated at 110° C. in the microwave for 30 minutes. The mixture was concentrated to half its original volume and washed with DCM. The aqueous phase was acidified to pH4 (2M HCl) and resulting precipitate collected, washed with water and dried under vacuum (172 mg, 76% Yield). 1H NMR (400.0 MHz, DMSO) d 7.41 (2H, br s), 7.69 (2H, m), 7.76 (1H, m), 7.98 (2H, m), 8.09 (2H, m), 8.29 (2H, m), 8.94 (1H, s); MS (ES+) 360.98

Workup

  1. customthe mixture de-gassed (×5)
  2. customThe reaction was de-gassed again
  3. concentrationThe mixture was concentrated to half its original volume
  4. washwashed with DCM
  5. customresulting precipitate
  6. customcollected
  7. washwashed with water
  8. customdried under vacuum (172 mg, 76% Yield)

Sources & evidence

ORD record
ord-53bfd5e705334097b60da95911f90c2e
Source dataset
uspto-grants-2016_06
Patent number
US09365557B2

Reaction notes

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