Hydrochloric Acid → 4-(6-Carbamoyl-3,5-dimethylpyrazin-2-yl)phenylboronic acid

HRID 1930126노트

반응식

HRID 1930126 반응식
I([O-])(=O)(=O)=O.[Na+].[CH3:7][C:8]1[C:9]([C:30]([NH2:32])=[O:31])=[N:10][C:11]([C:15]2[CH:20]=[CH:19][C:18]([B:21]3[O:25]C(C)(C)C(C)(C)[O:22]3)=[CH:17][CH:16]=2)=[C:12]([CH3:14])[N:13]=1.Cl>C1COCC1.O>[C:30]([C:9]1[N:10]=[C:11]([C:15]2[CH:16]=[CH:17][C:18]([B:21]([OH:25])[OH:22])=[CH:19][CH:20]=2)[C:12]([CH3:14])=[N:13][C:8]=1[CH3:7])(=[O:31])[NH2:32]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 23667635Sodium periodateHCID 596277103,5-Dimethyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazine-2-carboxamide2회

생성물 1

HCID 596277414-(6-Carbamoyl-3,5-dimethylpyrazin-2-yl)phenylboronic acid수율 86%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Sodium periodate (19.64 g, 91.81 mmol) was added in one portion to 3,5-dimethyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazine-2-carboxamide (Intermediate 7-6; 10.81 g, 30.60 mmol) in THF (320 mL) and water (80 mL) and the resulting cloudy suspension was stirred at ambient temperature for 30 minutes. 1M hydrochloric acid (21.42 mL, 21.42 mmol) was added and the resulting suspension was stirred at ambient temperature for 17 hours. The reaction mixture was evaporated and diluted with water (100 mL) and the precipitate was collected by filtration, washed with water (400 mL) and dried under vacuum at 65° C. over 4 hours to afford 4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenylboronic acid (7.13 g, 86%) as a white solid, which was used without further purification.

후처리

  1. stirringthe resulting suspension was stirred at ambient temperature for 17 hours
  2. customThe reaction mixture was evaporated
  3. additiondiluted with water (100 mL)
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with water (400 mL)
  6. customdried under vacuum at 65° C. over 4 hours

출처 및 근거

ORD 기록
ord-4ee18d6560b64a1bbf3796fb691b1f90
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188092B2

반응 노트

불러오는 중…