Diisopropylcarbodiimide → HCID 117622594, compound

HRID 56834Notes

Reaction equation

HRID 56834 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][CH2:21][O:22][C:23]([F:26])([F:25])[F:24])[C:17](O)=[O:18])[C:10](=[O:27])[CH:9]=2)[CH:7]=1.[NH2:30][C:31]1[CH:43]=[CH:42][C:34]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[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][CH2:21][O:22][C:23]([F:25])([F:26])[F:24])[C:17]([NH:30][C:31]3[CH:43]=[CH:42][C:34]([C:35]([O:37][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:36])=[CH:33][CH:32]=3)=[O:18])[C:10](=[O:27])[CH:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 117622593HCID 117622593, compound

Product 1

HCID 117622594HCID 117622594, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

330 mg (766 μmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4-(trifluoromethoxy)butanoic acid (racemate), 148 mg (766 μmol) of tert-butyl 4-aminobenzoate, 109 mg (766 μmol) of Oxima and 120 μl (766 μmol) of DIC in 7.7 ml of dimethylformamide were reacted according to General Method 5B. The crude product was purified by flash chromatography (40 g cartridge, 40 ml/min, cyclohexane/ethyl acetate gradient). Yield: 329 mg (64% of theory)

Workup

  1. customThe crude product was purified by flash chromatography (40 g cartridge, 40 ml/min, cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-f403d1775a264bb8b42f0fc634c4b2d0
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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