N-((2R)-2,3-Dihydroxypropoxy)-3,4-difluoro-2-((2-fluoro-4-iodophenyl)amino)benzamide → (S)-2,3-Dihydroxy-propoxyl-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-benzamide

HRID 1062297Notes

Reaction equation

HRID 1062297 reaction equation
CC1(C)[O:6][C@H:5]([CH2:7][O:8]N)[CH2:4][O:3]1.FC1C(NC2C=CC(I)=CC=2F)=C(C=CC=1F)C(O)=O.O[C@H](CO)CO[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:6][C@@H:5]([CH2:7][OH:8])[CH2:4][O:3][C:41]1[C:40]([F:43])=[C:39]([F:44])[C:38]([NH:45][C:46]2[CH:51]=[CH:50][C:49]([I:52])=[CH:48][C:47]=2[F:53])=[C:37]([CH:42]=1)[C:36]([NH2:35])=[O:54]

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 86759895(S)-2,3-Dihydroxy-propoxyl-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-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-95ff567397fe4bc38bb3eae2bf4b9481
Source dataset
uspto-grants-2005_11
Patent number
US06960614B2

Reaction notes

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