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1,2-Dichloroethane → N-(2-((4-acetyloxazol-2-yl)methyl)-2H-1,2,3-triazol-4-yl)-2-methyl-5-(m-tolyl)oxazole-4-carboxamide

HRID 82800
ノート
印刷プレビュー

反応式

HRID 82800 の反応式
N#N.[CH3:3][C:4]1[O:5][C:6]([C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=2)=[C:7]([C:9]([OH:11])=O)[N:8]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C.[NH2:42][C:43]1[CH:47]=[N:46][N:45]([CH2:48][C:49]2[O:50][CH:51]=[C:52]([C:54](=[O:56])[CH3:55])[N:53]=2)[N:44]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:54]([C:52]1[N:53]=[C:49]([CH2:48][N:45]2[N:44]=[C:43]([NH:42][C:9]([C:7]3[N:8]=[C:4]([CH3:3])[O:5][C:6]=3[C:12]3[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=3)=[O:11])[CH:47]=[N:46]2)[O:50][CH:51]=1)(=[O:56])[CH3:55]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 6

HCID 111,2-DichloroethaneHCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 669292052-Methyl-5-(m-tolyl)oxazole-4-carboxylic acidHCID 673655881-(2-((4-amino-2H-1,2,3-triazol-2-yl)methyl)oxazol-4-yl)ethanone

生成物 1

HCID 67967926
N-(2-((4-acetyloxazol-2-yl)methyl)-2H-1,2,3-triazol-4-yl)-2-methyl-5-(m-tolyl)oxazole-4-carboxamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒3 回

実験手順

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-methyl-5-(m-tolyl)oxazole-4-carboxylic acid (WO 2009/077990, p. 112) (590 mg, 2.72 mmol) in CH2Cl2 (20 mL) was treated at rt with DMAP (82 mg, 0.68 mmol), HOBt (441 mg, 3.62 mmol), EDC (1.3 g, 6.79 mmol) and DIPEA (1.8 mL, 10.86 mmol) and the resulting mixture was stirred for 30 min at rt. A solution of 1-(2-((4-amino-2H-1,2,3-triazol-2-yl)methyl)oxazol-4-yl)ethanone (WO 2009/077990, p. 105) (562 mg, 2.72 mmol) in CH2Cl2 (7.0 mL) was then added and the reaction mixture was stirred overnight at rt. The mixture was diluted with CH2Cl2 (50 mL), the org. phase was washed with water (50 mL), dried over MgSO4, filtered and the solvents were removed under reduced pressure. Purification of the residue by FC (4:6 hept-EA) gave the title compound as a white solid: TLC: rf (4:6 hept-EA)=0.35. LC-MS-conditions 07: tR=0.88 min, [M+H]+=407.05.

後処理

  1. stirringthe reaction mixture was stirred overnight at rt
  2. washphase was washed with water (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (4:6 hept-EA)

出典と根拠

ORDレコード
ord-fb7e4b9163634ffc8ba7be72eabedeb3
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846733B2

反応ノート

読み込み中…

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