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Methyl iodide → 2-{[2-Fluoro-5-(trifluoromethyl)phenylamino)-1-methylbenzimidazol-5-yl-oxy)pyridine-2-carboxylic acid

HRID 2070263
ノート
印刷プレビュー

反応式

HRID 2070263 の反応式
C([O:5][C:6]([C:8]1[CH:13]=[C:12](OC2C=CC(NC)=C(N)C=2)[CH:11]=[CH:10][N:9]=1)=[O:7])(C)(C)C.NC(N)=S.IC.C(OC(C1C=C([O:43][C:44]2[CH:65]=[CH:64][C:47]3[N:48]([CH3:63])[C:49]([NH:51][C:52]4[CH:57]=[C:56]([C:58]([F:61])([F:60])[F:59])[CH:55]=[CH:54][C:53]=4[F:62])=[N:50][C:46]=3[CH:45]=2)C=CN=1)=O)(C)(C)C.FC(F)(F)C(O)=O>CO.C(Cl)Cl>[F:62][C:53]1[CH:54]=[CH:55][C:56]([C:58]([F:61])([F:60])[F:59])=[CH:57][C:52]=1[NH:51][C:49]1[N:48]([CH3:63])[C:47]2[CH:64]=[CH:65][C:44]([O:43][C:8]3([C:6]([OH:7])=[O:5])[CH:13]=[CH:12][CH:11]=[CH:10][NH:9]3)=[CH:45][C:46]=2[N:50]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 6328Methyl iodideHCID 6422Trifluoroacetic acidHCID 2723790ThioureaHCID 22040526Tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylateHCID 86592200Tert-butyl4-(2-{[2-fluoro-5-(trifluoromethyl)phenyl)amino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylate

生成物 1

HCID 86592199
2-{[2-Fluoro-5-(trifluoromethyl)phenylamino)-1-methylbenzimidazol-5-yl-oxy)pyridine-2-carboxylic acid

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

To tert-butyl4-[3-amino-4-(methylamino)phenoxy]pyridine-2-carboxylate (1 eq) in methanol was added 2-fluoro-5-(trifluoromethyl)benzeneisothiocyanate (1 eq) and stir at ambient temperature for 16 h. Formation of the corresponding thiourea was followed by LC/MS. To it was then added iodomethane (1 eq) and heated to 60° C. for 2 h. Formation of tert-butyl4-(2-{[2-fluoro-5-(trifluoromethyl)phenyl]amino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylate was followed by LC/MS. To it in methylene chloride was added trifluoroacetic acid and stirred at ambient temperature overnight. Resulting 4-(2-{[2-fluoro-5-(trifluoromethyl)phenylamino)-1-methylbenzimidazol-5-yloxy)pyridine-2-carboxylic acid was purified by preparative chromatography. MS: MH+=446.

後処理

  1. stirringstirred at ambient temperature overnight

出典と根拠

ORDレコード
ord-0779765000154606b4204f9343097303
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08299108B2

反応ノート

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