Cesium carbonate → 4-({2-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4-hydroxybutanoyl}amino)benzoic acid

HRID 57033Notes

Reaction equation

HRID 57033 reaction equation
[Si]([O:18][CH2:19][CH2:20][CH:21]([N:36]1[CH:41]=[C:40]([O:42][CH3:43])[C:39]([C:44]2[CH:49]=[C:48]([Cl:50])[CH:47]=[CH:46][C:45]=2[C:51]#[N:52])=[CH:38][C:37]1=[O:53])[C:22]([NH:24][C:25]1[CH:35]=[CH:34][C:28]([C:29]([O:31]CC)=[O:30])=[CH:27][CH:26]=1)=[O:23])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CO.O>[Cl:50][C:48]1[CH:47]=[CH:46][C:45]([C:51]#[N:52])=[C:44]([C:39]2[C:40]([O:42][CH3:43])=[CH:41][N:36]([CH:21]([CH2:20][CH2:19][OH:18])[C:22]([NH:24][C:25]3[CH:35]=[CH:34][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=3)=[O:23])[C:37](=[O:53])[CH:38]=2)[CH:49]=1

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 123769555HCID 123769555, compound

Product 1

HCID 1176228784-({2-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4-hydroxybutanoyl}amino)benzoic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

266 mg (355 μmol) of ethyl 4-[(4-{[tert-butyl(diphenyl)silyl]oxy}-2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoyl)amino]benzoate (racemate) in 7 ml of methanol/water (4/1) were reacted with 232 mg (711 μmol) of caesium carbonate according to General Method 4. The crude product was purified by preparative HPLC [column: Chromatorex C18, 10 μm, 125 mm×30 mm, mobile phase: acetonitrile/0.05% formic acid gradient (0 to 3 min 10% acetonitrile, to 35 min 90% acetonitrile and a further 3 min 90% acetonitrile)]. Yield: 16.5 mg (9% of theory)

Workup

  1. customThe crude product was purified by preparative HPLC [column
  2. customa further 3 min 90% acetonitrile

Sources & evidence

ORD record
ord-8484528abf314baaaef188dfc75651d4
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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