1,1'-Carbonyldiimidazole → HCID 11385667, compound

HRID 917765Notes

Reaction equation

HRID 917765 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([I:20])[CH:17]=[CH:16][C:3]=1[NH:4][C:5]1[C:6]([C:13]([OH:15])=O)=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:33][CH2:34][CH:35]([OH:38])[CH2:36][OH:37]>C1COCC1.CN(C=O)C>[OH:38][CH:35]([CH2:36][OH:37])[CH2:34][NH:33][C:13]([C:6]1[C:5]([NH:4][C:3]2[CH:16]=[CH:17][C:18]([I:20])=[CH:19][C:2]=2[F:1])=[CH:10][C:9](=[O:11])[N:8]([CH3:12])[CH:7]=1)=[O:15]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 735613-Amino-1,2-propanediolHCID 112346084-(2-Fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid

Product 1

HCID 11385667HCID 11385667, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

4-(2-Fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid and CDI were dissolved in anhydrous THF/DMF (5:1) and treated with 3-amino-1,2-propandiol as for example 34. After workup, the residue was further purified by flash chromatography on silica gel (5% MeOH/CH2Cl2—10% MeOH/CH2Cl2 gradient elution) to give N-(2,3-dihydroxypropyl)-4-(2-fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide (33%) as a pale cream solid; m.p. (EtOAc/Hexane) 96-101° C. (glue-liquid). 1H NMR [400 MHz, CH3OD] δ 8.17 (s, 1H), 7.61 (dd, J=9.9, 1.9 Hz, 1H), 7.59-7.55 (m, 1H), 7.22 (t, J=8.4, 1H), 5.78 (s, 1H), 3.85-3.79 (m, 1H), 3.56 (dd, J=5.4, 2.3 Hz, 2H), 3.51 (s, 3H), 3.53-3.50 (m, 1H), 3.39-3.33 (m, 1H). HRMS (FAB+) calcd for C16H18FIN3O4 462.0326 (M+), found 462.0332. HPLC 84.8% (254 nm).

Workup

  1. customAfter workup, the residue was further purified by flash chromatography on silica gel (5% MeOH/CH2Cl2—10% MeOH/CH2Cl2 gradient elution)

Sources & evidence

ORD record
ord-a70b242e759d4cbf8a72693f6dc7d317
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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