4-Fluorobenzylamine → N-(4-fluorobenzyl)-2-(2-dimethylsulfamoylphenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

HRID 1822725Notes

Reaction equation

C(O[C:4]([C:6]1[N:7]=[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[S:21](=[O:26])(=[O:25])[N:22]([CH3:24])[CH3:23])[N:9]([CH3:14])[C:10](=[O:13])[C:11]=1[OH:12])=[O:5])C.[F:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH2:33])=[CH:30][CH:29]=1>>[F:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][NH:33][C:4]([C:6]2[N:7]=[C:8]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[S:21](=[O:26])(=[O:25])[N:22]([CH3:23])[CH3:24])[N:9]([CH3:14])[C:10](=[O:13])[C:11]=2[OH:12])=[O:5])=[CH:30][CH:29]=1

Participants

Reactant 2

HCID 673264-Fluorobenzylamine

HCID 546914412-(2-Dimethylsulfamoyl-phenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester

Product 1

HCID 54711182N-(4-fluorobenzyl)-2-(2-dimethylsulfamoylphenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide

Procedure

Prepared according to the procedure described for example 2 from 2-(2-dimethylsulfamoyl-phenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (0.076 g, 0.2mmol), and 4-fluorobenzylamine (0.11 mL, 1.0 mmol). The title product was obtained as white needles (0.0549 g, 60% yield). 1HNMR (500 MHz, CDCl3) δ: 12.08 (1H, s), 7.91 (1H, d, J=7.33 Hz), 7.71–7.66 (3H, m), 7.37 (1H, dd, J=7.32, 1.83 Hz), 7.22 (2H, q, J=5.50 Hz), 7.00 (2H, t, J=8.55 Hz), 4.62 (1H, dd, J=15.26, 7.02 Hz), 4.40 (1H, dd, J=14.64, 5.49 Hz), 3.23 (3H, s), 2.64 (6H, s). HRMS (ESI) calcd for C21H22FSN4O5 (M+H): 461.1295; found: 461.1300.

Workup

customPrepared

Sources & evidence

ORD record: ord-1be264e7ad094e15a8193550d1d161ba
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07037908B2

Reaction notes

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