N-(2,3-dihydroxypropoxy)-3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzamide → 5-Chloro-2-(2-chloro-4-iodo-phenylamino)-N-[(R)-2,3-dihydroxy-propoxy]-3,4-difluoro-benzamide

HRID 1062299Notes

Reaction equation

HRID 1062299 reaction equation
CC1(C)[O:6][C@@H:5]([CH2:7][O:8][NH2:9])[CH2:4][O:3]1.[Cl:11][C:12]1[C:13]([F:31])=[C:14]([F:30])[C:15]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=2[Cl:29])=[C:16]([CH:20]=1)[C:17](O)=[O:18].OC(CO)CONC(=O)C1C=CC(F)=C(F)C=1NC1C=CC(I)=CC=1F>C(O)C>[Cl:11][C:12]1[C:13]([F:31])=[C:14]([F:30])[C:15]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=2[Cl:29])=[C:16]([CH:20]=1)[C:17]([NH:9][O:8][CH2:7][C@H:5]([OH:6])[CH2:4][OH:3])=[O:18]

Participants

5

Reactant 3

HCID 10206158N-(2,3-dihydroxypropoxy)-3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzamideHCID 11298047(R)-O-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamineHCID 222859232-(2-Chloro4-iodophenylamino)-5-chloro-3,4-difluorobenzoic acid

Product 1

HCID 101286795-Chloro-2-(2-chloro-4-iodo-phenylamino)-N-[(R)-2,3-dihydroxy-propoxy]-3,4-difluoro-benzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared from (R)-O-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-hydroxylamine and 5-chloro-2-(2-chloro-4-iodo-phenylamino)-3,4-difluoro-benzoic acid by the procedure described for N-(2,3-dihydroxy-propoxy)-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-benzamide: m.p. 155-156° C.; [α]=−5.1° (c=3.5 mg/mL, ethanol); 1NMR (400 MHz, DMSO-d6) δ 12.03 (s, 1), 8.83 (s, 1H), 7.76 (s, 1H), 7.66 (d, 1H, J=6.8 Hz), 7.47 (d, 1H, J=8.5 Hz), 6.68 (t, 1H, J=6.6 Hz), 4.83 (bs, 1H), 4.60 (bs, 1H), 3.89-3.92 (m, 1H), 3.68-3.76 (m, 2H), 3.30 (2H, partially hidden by HDO); MS (APCI+)=533.0/535.0; Anal.calcd/found for C16H13Cl2F2IN2O4: C, 36.05/36.04; H, 2.46/2.25; N, 5.25/5.10; F, 7.13/7.18; Cl, 13.30, 13.50; I, 23.80, 24.02.

Sources & evidence

ORD record
ord-b0f8e33037b14ddea1d43e7a6d4722d3
Source dataset
uspto-grants-2005_11
Patent number
US06960614B2

Reaction notes

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