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 1292026노트

반응식

HRID 1292026 반응식
[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]

참가 물질

4

반응물 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

생성물 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-carboxamide수율 75.4%

시약·촉매·용매 1

HCID 24386Thionyl Chloride용매

실험 절차

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.

후처리

  1. temperaturecooling
  2. customevaporating to dryness

출처 및 근거

ORD 기록
ord-02bc4bbb3d9f4161bd866fa710d4628b
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05756496

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