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

HRID 658369노트

반응식

HRID 658369 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

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)]

후처리

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

출처 및 근거

ORD 기록
ord-23c2cedcabfb4a9b93d8d666e945beb3
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076486B2

반응 노트

불러오는 중…