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Sodium Carbonate → tert-butyl 4-(5-amino-6-(5-phenyl-1,2,4-oxadiazol-3-yl)pyrazin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 1959416
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HRID 1959416 반응식
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:24][C:25]([N:27]1[CH2:32][CH:31]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O.C(OCC)(=O)C>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:30]2[CH2:31][CH2:32][N:27]([C:25]([O:24][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:26])[CH2:28][CH:29]=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
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참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 594722055-Bromo-3-(5-phenyl-1,2,4-oxadiazol-3-yl)pyrazin-2-ylamine

생성물 1

HCID 66744707tert-butyl 4-(5-amino-6-(5-phenyl-1,2,4-oxadiazol-3-yl)pyrazin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate수율 88.6%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

실험 절차

5-bromo-3-(5-phenyl-1,2,4-oxadiazol-3-yl)pyrazin-2-amine (150 mg, 0.4715 mmol), tert-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate (189.5 mg, 0.6130 mmol) and sodium carbonate (707.0 μL of 2 M, 1.414 mmol) in DMF (1.500 mL) were heated to 120° C. for 45 min in the microwave. After this time the reaction mixture was diluted with water (5 mL) and ethyl acetate (5 mL) and the layers separated. Organic layer washed with water (3×5 mL), dried (MgSO4) and concentrated in vacuo to leave the title compound as a yellow/orange solid (175.6 mg, 88% yield). 1H NMR (400 MHz, DMSO) d 1.44 (s, 9H), 2.60 (m, 2H), 3.57 (m, 2H), 4.06 (m, 2H), 6.70 (s, 1H), 7.30 (br s, 2H), 7.69 (m, 2H), 7.77 (m, 1H), 8.25 (m, 2H) and 8.51 (1H, s) ppm; MS (ES+) 421.02

후처리

  1. customthe layers separated
  2. washOrganic layer washed with water (3×5 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d3732b0b0185482192fb0f6d8cdb175b
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08410112B2

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