N-((2R)-2,3-Dihydroxypropoxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide → N-[(2S)-2,3-Dihydroxypropoxy]-3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]benzamide

HRID 2218474Notes

Reaction equation

HRID 2218474 reaction equation
CC1(C)O[C@H](CON)CO1.FC1C(NC2C=CC(I)=CC=2F)=C(C=CC=1F)C(O)=O.[OH:31][C@H:32]([CH2:55][OH:56])[CH2:33][O:34][NH:35][C:36](=[O:54])[C:37]1[CH:42]=[CH:41][C:40]([F:43])=[C:39]([F:44])[C:38]=1[NH:45][C:46]1[CH:51]=[CH:50][C:49]([I:52])=[CH:48][C:47]=1[F:53]>CO>[OH:31][C@@H:32]([CH2:55][OH:56])[CH2:33][O:34][NH:35][C:36](=[O:54])[C:37]1[CH:42]=[CH:41][C:40]([F:43])=[C:39]([F:44])[C:38]=1[NH:45][C:46]1[CH:51]=[CH:50][C:49]([I:52])=[CH:48][C:47]=1[F:53]

Participants

5

Reactant 3

HCID 9826528N-((2R)-2,3-Dihydroxypropoxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamideHCID 14814202(S)-O-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamineHCID 220256632-(2-Fluoro-4-iodoanilino)-3,4-difluorobenzoic acid

Product 1

HCID 10152076N-[(2S)-2,3-Dihydroxypropoxy]-3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared from (S)-O-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-hydroxylamine and 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-benzoic acid by the procedure described above for N-[(R)-2,3-dihydroxy-propoxy]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-benzamide: m.p. 116-118° C. (Form II of Compound C); and m.p. 116-118° C. (Form I of Compound C); [α]=+1.77° (c=1.13, methanol). Analysis: Calcd. For: C16H14F3I1N2O4: C, 39.85; H, 2.93; N, 5.81; F, 11.82; I, 26.32. Found: C, 40.01; H, 2.73; N, 5.84; F, 11.45; I, 26.42.

Sources & evidence

ORD record
ord-67269d5cdcdc4c99afd9971c86abce5d
Source dataset
uspto-grants-2008_08
Patent number
US07411001B2

Reaction notes

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