Ethyl isocyanatoacetate → (3-{5-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-[1,3,4]oxadiazol-2-yl}-ureido)-acetic acid ethylester

HRID 658369ノート

反応式

HRID 658369 の反応式
[NH2:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[NH:13][C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=2[F:21])=[N:4][N:3]=1.[N:22]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:23]=[O:24].N(CC([O-])=O)=C=O>C1COCC1.C(OCC)C>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][NH:22][C:23]([NH:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][C:8]=2[NH:13][C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=2[F:21])=[N:4][N:3]=1)=[O:24])[CH3:30]

参加物

6

反応物 3

HCID 76283Ethyl isocyanatoacetateHCID 17747573[4-(5-Amino-[1,3,4]oxadiazol-2-yl)-pyridin-3-yl]-(2-fluoro-4-iodo-phenyl)-amineHCID 22220581Isocyanatoacetate

生成物 1

HCID 59026789(3-{5-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-[1,3,4]oxadiazol-2-yl}-ureido)-acetic acid ethylester収率 54.4%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A suspension of [4-(5-Amino-[1,3,4]oxadiazol-2-yl)-pyridin-3-yl]-(2-fluoro-4-iodo-phenyl)-amine (0.200 g, 0.504 mmol) in dry THF (3 mL) was treated with ethyl isocyanatoacetate (0.077 g, 0.596 mmol). The reaction mixture was stirred at RT overnight. More isocyanatoacetate (0.083 g, 0.643 mmol) was added, and the mixture was stirred for another 72 hrs. The material was diluted with diethyl ether (2 mL), filtered and dried under high vacuum for 2 h to afford a yellow solid product (0.144 g, 0.274 mmol, 54%) LC/MS (Method A) [5.53 min; 527(M+1)]

後処理

  1. stirringthe mixture was stirred for another 72 hrs
  2. filtrationfiltered
  3. customdried under high vacuum for 2 h

出典と根拠

ORDレコード
ord-23c2cedcabfb4a9b93d8d666e945beb3
出典データセット
uspto-grants-2011_12
特許番号
US08076486B2

反応ノート

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