Benzocaine → HCID 117622726, compound

HRID 56938Notes

Reaction equation

HRID 56938 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:30]#[N:31])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][CH:21]3[CH2:26][CH2:25][S:24](=[O:28])(=[O:27])[CH2:23][CH2:22]3)[C:17]([OH:19])=O)[C:10](=[O:29])[CH:9]=2)[CH:7]=1.[NH2:32][C:33]1[CH:43]=[CH:42][C:36]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:35][CH:34]=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:30]#[N:31])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:20][CH:21]3[CH2:26][CH2:25][S:24](=[O:28])(=[O:27])[CH2:23][CH2:22]3)[C:17]([NH:32][C:33]3[CH:34]=[CH:35][C:36]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:42][CH:43]=3)=[O:19])[C:10](=[O:29])[CH:9]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 2337BenzocaineHCID 12734DiisopropylcarbodiimideHCID 18373917Acetonitrile--water (1/1)HCID 117622931HCID 117622931, compound

Product 1

HCID 117622726HCID 117622726, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

768 mg (1.19 mmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)propanoic acid (racemate, purity 72%), 786 mg (4.76 mmol) of ethyl 4-aminobenzoate, 67.6 mg (476 μmol) of Oxima and 741 μl (4.76 mmol) of DIC in 11.5 ml of dimethylformamide were reacted according to General Method 5B. Preparative HPLC (acetonitrile/water gradient) gave the title compound. Yield: 331 mg (45% of theory)

Sources & evidence

ORD record
ord-c6df94c9391a48528f0c50ef3c1e7779
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

Loading…