Benzenemethanamine, 3-chloro-4-methyl- → HCID 54691447, compound

HRID 1822709Notes

Reaction equation

HRID 1822709 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[CH3:35])[CH2:30][NH2:31]>>[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[CH3:35])[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:23])=[O:24])[N:9]([CH3:14])[C:10](=[O:13])[C:11]=1[OH:12])=[O:5]

Participants

3

Reactant 2

HCID 106225Benzenemethanamine, 3-chloro-4-methyl-HCID 54691440HCID 54691440, compound

Product 1

HCID 54691447HCID 54691447, 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 (55.56 mg, 0.15 mmol) and 3-chloro-4-methylbenzylamine (107 mg, 0.75 mmol). The title product was obtained as a pink solid (58.6 mg, 81% yield). 1HNMR (500 MHz, CDCl3) δ: 12.12 (1H, s), 7.87 (1H, dd, J=7.63, 2.45 Hz), 7.53 (1H, t, J=5.50 Hz), 7.48 (1H, td, J=7.62, 2.74 Hz), 7.42 (1H, dd, J=8.24, 4.89 Hz), 7.20 (1H, s), 7.17 (1H, d, J=7.63 Hz), 7.05 (1H, d, J=7.63 Hz), 4.57 (1H, dd, J=14.95, 6.72 Hz), 4.43 (1H, dd, J=14.95, 5.49 Hz), 3.26 (3H, s), 3.05 (3H, s), 2.33 (3H, s). HRMS (ESI) calcd for C21H20ClFN3O5S (M+H): 480.0796; found: 480.0793.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-9737f8c944224cab9d1b813b92f49ae3
Source dataset
uspto-grants-2006_05
Patent number
US07037908B2

Reaction notes

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