Diisopropylcarbodiimide → HCID 117622852, compound

HRID 56813Notes

Reaction equation

HRID 56813 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:27]#[N:28])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][CH:21]3[CH2:23][C:22]3([F:25])[F:24])[C:17]([OH:19])=O)[C:10](=[O:26])[CH:9]=2)[CH:7]=1.[NH2:29][C:30]1[CH:42]=[CH:41][C:33]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[CH:32][CH:31]=1.CC(C)N=C=NC(C)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:27]#[N:28])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][CH:21]3[CH2:23][C:22]3([F:25])[F:24])[C:17]([NH:29][C:30]3[CH:42]=[CH:41][C:33]([C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])=[CH:32][CH:31]=3)=[O:19])[C:10](=[O:26])[CH:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 233272Benzoic acid, 4-amino-, 1,1-dimethylethyl esterHCID 117622688HCID 117622688, compound

Product 1

HCID 117622852HCID 117622852, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

88.0 mg (215 μmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-[2,2-difluorocyclopropyl]propanoic acid (mixture of two racemic diastereomers), 41.6 mg (215 μmol) of tert-butyl 4-aminobenzoate, 30.6 mg (215 μmol) of Oxima and 34.0 μl (215 μmol) of DIC in 2.1 ml of dimethylformamide were reacted according to General Method 5B. Yield: 101 mg (66% of theory)

Sources & evidence

ORD record
ord-fd7d0fcf163e4c9496ba22fd72caacea
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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