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

HRID 82853ノート

反応式

HRID 82853 の反応式
N#N.[CH3:3][C:4]1[O:5][C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=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.[CH3:41][O:42][CH2:43][C:44]1[N:45]=[C:46]([CH2:49][N:50]2[N:54]=[C:53]([NH2:55])[CH:52]=[N:51]2)[O:47][CH:48]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:41][O:42][CH2:43][C:44]1[N:45]=[C:46]([CH2:49][N:50]2[N:54]=[C:53]([NH:55][C:9]([C:7]3[N:8]=[C:4]([CH3:3])[O:5][C:6]=3[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:11])[CH:52]=[N:51]2)[O:47][CH:48]=1

参加物

9

反応物 6

HCID 111,2-DichloroethaneHCID 947NitrogenHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 156303442-Methyl-5-phenyl-1,3-oxazole-4-carboxylic acidHCID 679580862-((4-(Methoxymethyl)oxazol-2-yl)methyl)-2H-1,2,3-triazol-4-amine

生成物 1

HCID 57406926N-(2-((4-(Methoxymethyl)oxazol-2-yl)methyl)-2H-1,2,3-triazol-4-yl)-2-methyl-5-phenyloxazole-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-phenyloxazole-4-carboxylic acid (WO 2009/077990, p. 113) (955 mg, 4.70 mmol) in CH2Cl2 (27 mL) was treated at rt with DMAP (143 mg, 1.17 mmol), HOBt (763 mg, 5.65 mmol), EDC (2.25 g, 11.75 mmol) and DIPEA (3.22 mL, 18.80 mmol) and the resulting mixture was stirred for 45 min at rt. A solution of 2-((4-(methoxymethyl)oxazol-2-yl)methyl)-2H-1,2,3-triazol-4-amine (983 mg, 4.70 mmol) in CH2Cl2 (20 mL) was then added and the reaction mixture was stirred overnight at rt. The mixture was diluted with CH2Cl2 (40 mL), the layers were separated and the org. phase was washed with water (40 mL), dried over MgSO4, filtered and the solvents were removed under reduced pressure. Purification of the residue by crystallization for EA to give the title compound as a white solid: TLC: rf (4:6 hept-EA)=0.14. LC-MS-conditions 07: tR=0.84 min, [M+H]+=395.44.

後処理

  1. stirringthe reaction mixture was stirred overnight at rt
  2. customthe layers were separated
  3. washphase was washed with water (40 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue
  8. customby crystallization for EA

出典と根拠

ORDレコード
ord-baf7511a72d94cb7929451ef04486d3d
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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