5-(4-Aminophenyl)-1,3-oxazol-2(3H)-one → HCID 117622778, compound

HRID 57048Notes

Reaction equation

HRID 57048 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:26]#[N:27])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][CH:21]3[CH2:24][CH2:23][CH2:22]3)[C:17](O)=[O:18])[C:10](=[O:25])[CH:9]=2)[CH:7]=1.[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[O:39][C:38](=[O:40])[NH:37][CH:36]=2)=[CH:31][CH:30]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:26]#[N:27])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][CH:21]3[CH2:24][CH2:23][CH2:22]3)[C:17]([NH:28][C:29]3[CH:30]=[CH:31][C:32]([C:35]4[O:39][C:38](=[O:40])[NH:37][CH:36]=4)=[CH:33][CH:34]=3)=[O:18])[C:10](=[O:25])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 1176227935-(4-Aminophenyl)-1,3-oxazol-2(3H)-oneHCID 1176228532-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-cyclobutylpropanoic acid

Product 1

HCID 117622778HCID 117622778, compound

Procedure

103 mg (purity 94%, 0.25 mmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-cyclobutylpropanoic acid (racemate) and 55 mg (0.28 mmol, 1.1 eq.) of 5-(4-aminophenyl)-1,3-oxazol-2(3H)-one were reacted according to General Method 1. The crude product was purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 36 mg (27% of theory)

Workup

  1. customThe crude product was purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Sources & evidence

ORD record
ord-9729ecca1af54e5591291a160be1833f
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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