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Water → 3-(5-Aminopyrazin-2-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

HRID 629054
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HRID 629054 반응식
Br[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)=[O:6].CC1(C)C(C)(C)OB([C:30]2[N:31]=[CH:32][C:33]([NH2:36])=[N:34][CH:35]=2)O1.C([O-])([O-])=O.[Na+].[Na+].O>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.COCCOC>[NH2:36][C:33]1[N:34]=[CH:35][C:30]([C:2]2[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=2)[C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)=[O:6])=[N:31][CH:32]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 13710333-bromo-N-(4-(trifluoromethoxy)phenyl)benzamideHCID 179989875-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amine

생성물 1

HCID 722028783-(5-Aminopyrazin-2-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 80711,2-Dimethoxyethane용매

실험 절차

3-Bromo-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 3.1, 50 mg, 0.139 mmol), 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazin-2-amine (0.180 mmol), 2 M Na2CO3 (0.104 mL, 0.208 mmol), (Ph3P)4Pd (8 mg, 6.94 μmol), water (0.8 mL) and DME (2.4 mL) were added to a vial, which was sealed and subjected to MW irradiation at 150° C. for 10 min. The RM was filtered through a PL-Thiol MP SPE cartridge (StratoSpheres™, 6 mL) and the cartridge was washed with MeOH (10 mL). The combined filtrates were evaporated to dryness under reduced pressure and the crude product was purified by preparative HPLC to afford the title compound. UPLC-MS (Condition 6) tR=1.84 min, m/z=375.3 [M+H]+.

후처리

  1. customwas sealed
  2. customsubjected to MW irradiation at 150° C. for 10 min
  3. filtrationThe RM was filtered through a PL-Thiol MP SPE cartridge (StratoSpheres™, 6 mL)
  4. washthe cartridge was washed with MeOH (10 mL)
  5. customThe combined filtrates were evaporated to dryness under reduced pressure
  6. customthe crude product was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-4f33e558f5434e308935840b836f511a
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09315489B2

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