4-[2-methyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]benzoic Acid → N-[4-(2-Dimethylaminoethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-6-yl]-2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxamide

HRID 1292026ノート

反応式

HRID 1292026 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[C:11]([CH3:13])[O:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20](O)=[O:21])=[CH:16][CH:15]=1.[NH2:23][C:24]1[CH:25]=[CH:26][C:27]2[O:32][CH2:31][C:30](=[O:33])[N:29]([CH2:34][CH2:35][N:36]([CH3:38])[CH3:37])[C:28]=2[CH:39]=1>S(Cl)(Cl)=O>[CH3:37][N:36]([CH3:38])[CH2:35][CH2:34][N:29]1[C:28]2[CH:39]=[C:24]([NH:23][C:20]([C:17]3[CH:18]=[CH:19][C:14]([C:3]4[CH:4]=[CH:5][C:6]([C:8]5[N:12]=[C:11]([CH3:13])[O:10][N:9]=5)=[CH:7][C:2]=4[CH3:1])=[CH:15][CH:16]=3)=[O:21])[CH:25]=[CH:26][C:27]=2[O:32][CH2:31][C:30]1=[O:33]

参加物

4

反応物 2

HCID 111301684-[2-methyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]benzoic AcidHCID 189140886-amino-4-[2-(dimethylamino)ethyl]-3,4-dihydro-2H-1,4-benzoxazin-3-one

生成物 1

HCID 18914075N-[4-(2-Dimethylaminoethyl)-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-6-yl]-2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxamide収率 75.4%

試薬・触媒・溶媒 1

HCID 24386Thionyl Chloride溶媒

実験手順

2'-Methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxylic acid (EP 0553268A1) (0.188 g, 0.64 mmol) was converted to the acyl chloride by stirring at reflux under Ar in thionyl chloride (10 ml) for 45 min, cooling, and then evaporating to dryness. This was reacted with 6-amino-4(2-dimethylaminoethyl)-1,4-benzoxazin-3(4H)-one (D8) (0.150 g, 0.64 mmol) following the procedure of Example 1. This gave the title compound (0.247 g, 75%) as a white foam, which was converted to the oxalate, a white solid.

後処理

  1. temperaturecooling
  2. customevaporating to dryness

出典と根拠

ORDレコード
ord-02bc4bbb3d9f4161bd866fa710d4628b
出典データセット
uspto-grants-1998_05
特許番号
US05756496

反応ノート

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