4-Chlorobenzohydrazide → 4-Chloro-N'-((2R,3R)-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoyl)benzohydrazide

HRID 470766Notes

Reaction equation

HRID 470766 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[Cl:12][C:13]1[C:14]([CH3:29])=[C:15]([NH:21][C@H:22]([C@H:26]([OH:28])[CH3:27])[C:23](O)=[O:24])[CH:16]=[CH:17][C:18]=1[C:19]#[N:20]>>[C:6]([NH:8][NH2:9])(=[O:7])[C:5]1[CH:10]=[CH:11][CH:2]=[CH:3][CH:4]=1.[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH:9][C:23](=[O:24])[C@H:22]([NH:21][C:15]2[CH:16]=[CH:17][C:18]([C:19]#[N:20])=[C:13]([Cl:12])[C:14]=2[CH3:29])[C@H:26]([OH:28])[CH3:27])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 108164-ChlorobenzohydrazideHCID 57908625(2R,3R)-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoic acid

Product 2

HCID 11955BenzoylhydrazineHCID 670059594-Chloro-N'-((2R,3R)-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoyl)benzohydrazideYield 168.6%

Procedure

4-Chloro-N′(2R,3R)-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoyl)benzohydrazide was prepared using 4-chlorobenzoic hydrazide (4.42 mmol, 1.1 equiv.) and (2R,3R)-2-(3-chloro-4-cyano-2-methylphenylamino)-3-hydroxybutanoic acid (4.02 mmol, 1.0 equiv.) according to the procedure as described for intermediate 5a. The crude off-white solid was recrystallized using hot methylene chloride to provide the desired product as a white solid (1.57 g, 93% yield). Other data: 1H NMR (400 MHz, acetone-d6, δ in ppm) 9.94 (br. s, 1H), 9.48 (br. s, 1H), 7.95 (d, J=8.5 Hz, 2H), 7.55 (m, 3H), 6.73 (d, J=8.5 Hz, 1H), 5.59 (br. d., J=7.1 Hz, 1H), 4.25 (m, 1H), 4.13 (m, 1H), 2.35 (s, 3H), 1.37 (d, J=6.4 Hz, 3H); LRMS (ESI+) exact mass calcd for C19H18Cl2N4O3 [M]+ 421.28, found 421.3; TLC Rf=0.32, 100% EtOAc, vanillin stain.

Workup

  1. customThe crude off-white solid was recrystallized

Sources & evidence

ORD record
ord-2e4e23fab3ac4e28a074dae1d12a3061
Source dataset
uspto-grants-2014_01
Patent number
US08629167B2

Reaction notes

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