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

HRID 658369Notes

Reaction equation

HRID 658369 reaction equation
[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]

Participants

6

Reactant 3

HCID 76283Ethyl isocyanatoacetateHCID 17747573HCID 17747573, compoundHCID 22220581Isocyanatoacetate

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

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)]

Workup

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

Sources & evidence

ORD record
ord-23c2cedcabfb4a9b93d8d666e945beb3
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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