Diisopropylcarbodiimide → HCID 136930240, compound

HRID 57040Notes

Reaction equation

HRID 57040 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:28]#[N:29])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][C:21]3([CH2:25][CH3:26])[CH2:24][O:23][CH2:22]3)[C:17]([OH:19])=O)[C:10](=[O:27])[CH:9]=2)[CH:7]=1.[NH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[NH:41][C:40](=[O:42])[O:39][N:38]=2)=[CH:33][CH:32]=1.CC(C)N=C=NC(C)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:28]#[N:29])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][C:21]3([CH2:25][CH3:26])[CH2:22][O:23][CH2:24]3)[C:17]([NH:30][C:31]3[CH:32]=[CH:33][C:34]([C:37]4[NH:41][C:40](=[O:42])[O:39][N:38]=4)=[CH:35][CH:36]=3)=[O:19])[C:10](=[O:27])[CH:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 117622973HCID 117622973, compoundHCID 1354531853-(4-Aminophenyl)-1,2,4-oxadiazol-5(2H)-one

Product 1

HCID 136930240HCID 136930240, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

37.4 mg (89.6 μmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-ethyloxetan-3-yl)propanoic acid (racemate), 15.9 mg (89.6 μmol) of 3-(4-aminophenyl)-1,2,4-oxadiazol-5(4H)-one, 12.7 mg (89.6 μmol) of Oxima and 14.0 μl (89.6 μmol) of DIC in 950 μl of dimethylformamide were reacted according to General Method 5. The crude product was purified by preparative HPLC [column: Chromatorex C18, 10 nm, 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)] and then using Method 10. Yield: 2 mg (4% 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-7d42fe3a6a9d469094237ea00fc8e288
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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