1H-Benzimidazole-2-carboxylic acid, 6-amino-, ethyl ester → Ethyl 6-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoyl}amino)-1H-benzimidazole-2-carboxylate

HRID 56762Notes

Reaction equation

HRID 56762 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:27]=[CH:28][C:29]2[N:33]=[C:32]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[NH:31][C:30]=2[CH:39]=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]4[N:33]=[C:32]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[NH:31][C:30]=4[CH:39]=3)=[O:19])[C:10](=[O:22])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 450897201H-Benzimidazole-2-carboxylic acid, 6-amino-, ethyl esterHCID 1176225692-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid

Product 1

HCID 117622570Ethyl 6-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoyl}amino)-1H-benzimidazole-2-carboxylate

Procedure

87 mg (0.25 mmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid (racemate) and 56 mg (0.28 mmol, 1.1 eq.) of ethyl 6-amino-1H-benzimidazole-2-carboxylate were reacted according to General Method 5A. The crude product was purified by preparative HPLC (Reprosil C18, acetonitrile/water+0.1% formic acid gradient). Yield: 86 mg (64% of theory)

Workup

  1. customThe crude product was purified by preparative HPLC (Reprosil C18, acetonitrile/water+0.1% formic acid gradient)

Sources & evidence

ORD record
ord-4bbf5adf92fb485584c7dd69008566a9
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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