Benzenemethanamine, 3,4-dichloro- → HCID 54711750, compound

HRID 1822707Notes

Reaction equation

HRID 1822707 reaction equation
C(O[C:4]([C:6]1[N:7]=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[S:22]([CH3:25])(=[O:24])=[O:23])[N:9]([CH3:14])[C:10](=[O:13])[C:11]=1[OH:12])=[O:5])C.[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:30][NH2:31]>>[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:30][NH:31][C:4]([C:6]1[N:7]=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[S:22]([CH3:25])(=[O:24])=[O:23])[N:9]([CH3:14])[C:10](=[O:13])[C:11]=1[OH:12])=[O:5]

Participants

3

Reactant 2

HCID 1608Benzenemethanamine, 3,4-dichloro-HCID 54691440HCID 54691440, compound

Product 1

HCID 54711750HCID 54711750, compound

Procedure

Prepared according to the procedure described for example 2 from 2-(4-fluoro-2-methanesulfonyl-phenyl)-5-hydroxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (74.07 mg, 0.20 mmol) and 3,4-dichlorobenzylamine (132 mg, 0.75 mmol). The title product was obtained as a pink solid (69 mg, 92% yield). 1HNMR (500 MHz, CDCl3) δ: 12.00 (1H, s), 7.87 (1H, dd, J=7.63, 2.45 Hz), 7.60 (1H, t, J=7.60 Hz), 7.50–7.42 (2H, m), 7.39 (1H, d, J=7.93 Hz), 7.32 (1H, s), 7.11 (1H, d, J=7.32 Hz), 4.55 (1H, dd, J=15.26, 6.41 Hz), 4.49 (1H, dd, J=15.26, 6.10 Hz), 3.26 (3H, s), 3.06 (3H, s). HRMS (ESI) calcd for C20H17Cl2FN3O5S (M+H): 500.0250; found: 500.0259.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-b178cf4c51f44f56959eb362469dec6d
Source dataset
uspto-grants-2006_05
Patent number
US07037908B2

Reaction notes

Loading…