1,2-Dichloroethane → N-(2-((2-(methoxymethyl)thiazol-5-yl)methyl)-2H-1,2,3-triazol-4-yl)-5-phenyloxazole-4-carboxamide

HRID 82796ノート

反応式

HRID 82796 の反応式
N#N.[C:3]1([C:9]2[O:13][CH:12]=[N:11][C:10]=2[C:14]([OH:16])=O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C.[CH3:40][O:41][CH2:42][C:43]1[S:44][C:45]([CH2:48][N:49]2[N:53]=[C:52]([NH2:54])[CH:51]=[N:50]2)=[CH:46][N:47]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:40][O:41][CH2:42][C:43]1[S:44][C:45]([CH2:48][N:49]2[N:53]=[C:52]([NH:54][C:14]([C:10]3[N:11]=[CH:12][O:13][C:9]=3[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[O:16])[CH:51]=[N:50]2)=[CH:46][N:47]=1

参加物

9

反応物 6

HCID 111,2-DichloroethaneHCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27762995-Phenyl-1,3-oxazole-4-carboxylic acidHCID 679581002-((2-(methoxymethyl)thiazol-5-yl)methyl)-2H-1,2,3-triazol-4-amine

生成物 1

HCID 86698198N-(2-((2-(methoxymethyl)thiazol-5-yl)methyl)-2H-1,2,3-triazol-4-yl)-5-phenyloxazole-4-carboxamide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 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 commercially available 5-phenyloxazole-4-carboxylic acid (30.0 mg, 0.16 mmol) in CH2Cl2 (1.0 mL) was treated at rt with DMAP (4.8 mg, 0.04 mmol), HOBt (26 mg, 0.19 mmol), EDC (76 mg, 0.40 mmol) and DIPEA (0.11 mL, 0.63 mmol) and the resulting mixture was stirred for 30 min at rt. A solution of 2-((2-(methoxymethyl)thiazol-5-yl)methyl)-2H-1,2,3-triazol-4-amine (36 mg, 0.16 mmol) in CH2Cl2 (0.6 mL) was then added and the reaction mixture was stirred overnight at rt. The solvents were removed under reduced pressure. Purification of the residue by HPLC gave the title compound as a beige solid. TLC: rf (4:6 hept-EA)=0.30. LC-MS-conditions 07: tR=0.87 min, [M+H]+=397.39.

後処理

  1. stirringthe reaction mixture was stirred overnight at rt
  2. customThe solvents were removed under reduced pressure
  3. customPurification of the residue by HPLC

出典と根拠

ORDレコード
ord-6ad4906a996041d6a07dfc22ee3eff5c
出典データセット
uspto-grants-2014_09
特許番号
US08846733B2

反応ノート

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