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2-Furancarboxylic acid, hydrazide → 4-[5-amino-6-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N,N-dimethyl-benzamide

HRID 78611
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HRID 78611 반응식
BrP(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2:22][C:23]1[C:24]([C:40]([OH:42])=O)=[N:25][C:26]([C:29]2[CH:34]=[CH:33][C:32]([C:35](=[O:39])[N:36]([CH3:38])[CH3:37])=[CH:31][CH:30]=2)=[CH:27][N:28]=1.[O:43]1[CH:47]=[CH:46][CH:45]=[C:44]1[C:48]([NH:50][NH2:51])=O.CCN(C(C)C)C(C)C>C(#N)C>[NH2:22][C:23]1[N:28]=[CH:27][C:26]([C:29]2[CH:30]=[CH:31][C:32]([C:35]([N:36]([CH3:37])[CH3:38])=[O:39])=[CH:33][CH:34]=2)=[N:25][C:24]=1[C:40]1[O:42][C:48]([C:44]2[O:43][CH:47]=[CH:46][CH:45]=2)=[N:50][N:51]=1
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참가 물질

6

반응물 4

HCID 187312-Furancarboxylic acid, hydrazideHCID 70579Triphenylphosphine dibromideHCID 81531DiisopropylethylamineHCID 594717503-Amino-6-[4-(dimethylcarbamoyl)phenyl]pyrazine-2-carboxylic acid

생성물 1

HCID 594717054-[5-amino-6-[5-(2-furyl)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N,N-dimethyl-benzamide수율 51.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Dibromo(triphenyl)phosphorane was added to a solution of 3-amino-6-[4-(dimethylcarbamoyl)phenyl]pyrazine-2-carboxylic acid (100 mg, 0.35 mmol) and furan 2-carbohydrazide (44.1 mg, 0.35 mmol) in acetonitrile (3.0 mL) at room temperature. Bright yellow solution observed. The resulting solution was stirred at room temperature for 30 min. After this time, DIPEA (304 μL, 1.75 mmol) was added dropwise and the reaction mixture stirred at room temperature for 30 min. The reaction mixture was filtered to leave a yellow solid. The solid was purified by reverse phase preparative HPLC [Waters Sunfire C18, mM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. Product fractions were freeze dried to give the product as a yellow solid (67.6 mg, 51% yield); 1H NMR (400.0 MHz, DMSO) d 2.97 (m, 6H), 6.87 (m, 1H), 7.54-7.56 (m, 3H), 7.57 (br s, 2H), 8.15 (m, 3H) and 8.98 (1H, s) ppm; MS (ES+) 377.17

후처리

  1. stirringthe reaction mixture stirred at room temperature for 30 min
  2. filtrationThe reaction mixture was filtered
  3. customto leave a yellow solid
  4. customThe solid was purified by reverse phase preparative HPLC [Waters Sunfire C18
  5. waitmM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]
  6. customdried

출처 및 근거

ORD 기록
ord-9dcc33133ba44249b8e88fd2a1406d63
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08841308B2

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