Tris(hydroxymethyl)aminomethane → HCID 11191054, compound

HRID 917767Notes

Reaction equation

HRID 917767 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][C:34]([CH2:39][OH:40])([CH2:37][OH:38])[CH2:35][OH:36].CCCCCC>C1COCC1.CN(C=O)C>[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]([NH:33][C:34]([CH2:39][OH:40])([CH2:37][OH:38])[CH2:35][OH:36])=[O:15])=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=1

Participants

6

Reactant 4

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 8058HexaneHCID 682631,1'-CarbonyldiimidazoleHCID 112346084-(2-Fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid

Product 1

HCID 11191054HCID 11191054, compoundYield 22%

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 (4:1) and treated with 2-amino-2-[hydroxymethyl]-1,3-propandiol as for example 34. After the standard workup, trituration with hexane gave 4-(2-fluoro-4-iodoanilino)-N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide (22%) as a yellow/cream solid; m.p. (EtOAc/Hexane) 100-105° C. (glue-liquid). 1H NMR [400 MHz, (CD3)2SO] δ 9.62 (br s, 1H), 8.15 (s, 1H), 7.73 (dd, J=10.2, 1.7 Hz, 1H), 7.57 (d, J=8.5 Hz, 1H), 7.32 (s, 1H), 7.26 (t, J=8.5 Hz, 1H), 5.54 (s, 1H), 4.59 (t, J=5.7 Hz, 3H), 3.68 (d, J=5.7 Hz, 6H), 3.37 (s, 3H). HPLC 78.1% (254 nm). HRMS (FAB+) cald for C17H20FIN3O5 492.043 (M+), found 492.0425.

Sources & evidence

ORD record
ord-96f5c66304884f26a09930e78e82cf91
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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