N-Methylbenzylamine → HCID 68955474, compound

HRID 1784919Notes

Reaction equation

HRID 1784919 reaction equation
[CH3:1][N:2]([C:7]1[CH:8]=[C:9]([C:17]([O:19]C)=O)[CH:10]=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13])[S:3]([CH3:6])(=[O:5])=[O:4].C(Cl)CCl.[CH:25]1[CH:26]=[CH:27][C:28]2N(O)N=N[C:29]=2[CH:30]=1.[CH3:35][CH2:36][N:37](C(C)C)C(C)C.CNCC1C=CC=CC=1>>[CH3:1][N:2]([C:7]1[CH:16]=[C:11]([CH:10]=[C:9]([C:17](=[O:19])[NH:37][CH:36]([C:29]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:30]=2)[CH3:35])[CH:8]=1)[C:12]([O:14][CH3:15])=[O:13])[S:3]([CH3:6])(=[O:4])=[O:5]

Participants

4

Reactant 3

HCID 7669N-MethylbenzylamineHCID 11324067Dimethyl 5-(N-methylmethylsulfonamido)isophthalateHCID 86583922HCID 86583922, compound

Product 1

HCID 68955474HCID 68955474, compound

Procedure

Dimethyl 5-aminoisophthalate was mesylated by treating with methane sulfonylchloride and pyridine in dichloromethane. Then N-alkylation with methyl iodide under NaH/DMF condition gave dimethyl 5-(N-methylmethylsulfonamnido)isophthalate. Selective hydrolysis of dimethyl 5-(N-methylmethylsulfonamido)isophthalate, followed by EDC/HOBT/DIPEA mediated coupling with cc-methylbezylamine provided methyl 3-(N-methylmethylsulfonamido)-5-(1-phenylethylcarbamoyl)benzoate. Ester hydrolysis using aq. 1N NaOH in presence of THF/MeOH provided pure 3-(N-methylmethylsulfonamido)-5-(1-phenylethylcarbamoyl)benzoic acid as white solid.

Sources & evidence

ORD record
ord-0ca783e74b7f4afda7fdf29c9133cd08
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

Loading…