2-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid → HCID 178454441, compound

HRID 57073Notes

Reaction equation

HRID 57073 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:23]#[N:24])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][CH3:21])[C:17]([OH:19])=O)[C:10](=[O:22])[CH:9]=2)[CH:7]=1.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[NH:33][C:34]([C:37]([F:46])([F:45])[C:38]([F:44])([F:43])[C:39]([O:41][CH3:42])=[O:40])=[N:35][N:36]=2)=[CH:28][CH:27]=1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:23]#[N:24])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][CH3:21])[C:17]([NH:25][C:26]3[CH:27]=[CH:28][C:29]([C:32]4[NH:33][C:34]([C:37]([F:46])([F:45])[C:38]([F:44])([F:43])[C:39]([O:41][CH3:42])=[O:40])=[N:35][N:36]=4)=[CH:30][CH:31]=3)=[O:19])[C:10](=[O:22])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 1176225692-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acidHCID 178501026HCID 178501026, compound

Product 1

HCID 178454441HCID 178454441, compound

Procedure

87 mg (0.25 mmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid (racemate) and 88 mg (0.28 mmol, 1.1 eq.) of methyl 3-[5-(4-aminophenyl)-4H-1,2,4-triazol-3-yl]-2,2,3,3-tetrafluoropropanoate were reacted according to General Method 1. The crude product was purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 96 mg (purity 94%, 56% of theory)

Workup

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

Sources & evidence

ORD record
ord-b737bb51850b4373b14a88a0c9c4a397
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

Loading…