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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
ノート
印刷プレビュー

反応式

HRID 78611 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-9dcc33133ba44249b8e88fd2a1406d63
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08841308B2

反応ノート

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