Diisopropylcarbodiimide → Allyl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-methyloxetan-3-yl)propanoyl}amino)benzoate

HRID 56888Notes

Reaction equation

HRID 56888 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][C:21]3([CH3:25])[CH2:24][O:23][CH2:22]3)[C:17]([OH:19])=O)[C:10](=[O:26])[CH:9]=2)[CH:7]=1.[NH2:29][C:30]1[CH:41]=[CH:40][C:33]([C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35])=[CH:32][CH:31]=1.CC(C)N=C=NC(C)C.C(#N)C.O>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][C:21]3([CH3:25])[CH2:22][O:23][CH2:24]3)[C:17]([NH:29][C:30]3[CH:31]=[CH:32][C:33]([C:34]([O:36][CH2:37][CH:38]=[CH2:39])=[O:35])=[CH:40][CH:41]=3)=[O:19])[C:10](=[O:26])[CH:9]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 13075143Prop-2-en-1-yl 4-aminobenzoateHCID 18373917Acetonitrile--water (1/1)HCID 1176229772-[4-(5-Chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-methyloxetan-3-yl)propanoic acid

Product 1

HCID 117622716Allyl 4-({2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-methyloxetan-3-yl)propanoyl}amino)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

115 mg (285 μmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-methyloxetan-3-yl)propanoic acid (racemate), 51 mg (285 μmol) of allyl 4-aminobenzoate, 40.6 mg (285 μmol) of Oxima and 45 μl (0.29 mmol) of DIC in 2 ml of dimethylformamide were reacted according to General Method 5B. Preparative HPLC (acetonitrile/water gradient) gave the title compound. Yield: 25 mg (16% of theory)

Sources & evidence

ORD record
ord-1be502e86bd244e4b6544ad3b222d4d2
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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