Diisopropylcarbodiimide → HCID 117622331, compound

HRID 56905Notes

Reaction equation

HRID 56905 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:24]#[N:25])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH:20]([CH3:22])[CH3:21])[C:17](O)=[O:18])[C:10](=[O:23])[CH:9]=2)[CH:7]=1.[NH2:26][C:27]1[CH:28]=[CH:29][C:30]2[N:34]=[C:33]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[NH:32][C:31]=2[CH:40]=1.CC(C)N=C=NC(C)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:24]#[N:25])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH:20]([CH3:21])[CH3:22])[C:17]([NH:26][C:27]3[CH:28]=[CH:29][C:30]4[N:34]=[C:33]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[NH:32][C:31]=4[CH:40]=3)=[O:18])[C:10](=[O:23])[CH:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 450897201H-Benzimidazole-2-carboxylic acid, 6-amino-, ethyl esterHCID 117622540HCID 117622540, compound

Product 1

HCID 117622331HCID 117622331, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (277 μmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-methylbutanoic acid (racemate), 57 mg (277 μmol, 1.0 eq.) of ethyl 6-amino-1H-benzimidazole-2-carboxylate, 39.4 mg (277 μmol) of Oxima and 42.9 μl (277 μmol) of DIC in 5.4 ml of dimethylformamide were reacted according to General Method 5B. The crude product was purified by flash chromatography (silica gel 50, cyclohexane/ethyl acetate mixtures). Yield: 139 mg (91% of theory)

Workup

  1. customThe crude product was purified by flash chromatography (silica gel 50, cyclohexane/ethyl acetate mixtures)

Sources & evidence

ORD record
ord-d40b8bf71ef048ce859a54bd86a37b94
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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