1,1'-Carbonyldiimidazole → HCID 59026792, compound

HRID 658377Notes

Reaction equation

HRID 658377 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:18]=[N:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=O.N1(C(N2C=CN=C2)=O)C=CN=C1.[CH2:31]([O:33][C:34](=[O:39])[C:35]([NH:37]O)=[NH:36])[CH3:32]>CN(C=O)C.O>[CH2:31]([O:33][C:34]([C:35]1[N:37]=[C:12]([C:11]2[CH:15]=[CH:16][N:17]=[CH:18][C:10]=2[NH:9][C:3]2[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=2[F:1])[O:14][N:36]=1)=[O:39])[CH3:32]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 590267913-((2-Fluoro-4-iodophenyl)amino)isonicotinic acidHCID 178472862HCID 178472862, compound

Product 1

HCID 59026792HCID 59026792, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A reaction mixture of 3-(2-Fluoro-4-iodo-phenylamino)-isonicotinic acid (1000 mg, 2.79 mmol, 1.00 eq), and Di-imidazol-1-yl-methanone ((543 mg, 3.35 mmol, 1.20 eq) in DMF was stirred for 4 hrs at RT under argon. Then hydroxyamino-imino-acetic acid ethyl ester (612 mg, 4.19 mmol, 1.5 eq.) was added and the reaction mixture was stirred overnight, and then diluted with water. A yellow precipitate was formed that was filtered to afford the product (785 mg). [5.46 min; 455 (M+1)]

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customA yellow precipitate was formed
  3. filtrationthat was filtered

Sources & evidence

ORD record
ord-fe79a50fbf9e48fb9901f50a0b6efd9d
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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