4-Fluorobenzylamine → HCID 54676263, compound

HRID 1822706Notes

Reaction equation

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

Participants

Reactant 2

HCID 673264-Fluorobenzylamine

HCID 54691440HCID 54691440, compound

Product 1

HCID 54676263HCID 54676263, 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 4-fluorobenzylamine (125 mg, 1.0 mmol). The title product was obtained as a white solid (61 mg, 68% yield). 1HNMR (500 MHz, CDCl3) δ: 12.16 (1H, s), 7.87 (1H, dd, J=7.78, 2.59 Hz), 7.53 (1H, t, J 5.50 Hz), 7.48 (1H, td, J=7.86, 2.65 Hz), 7.41 (1H, dd, J=8.54, 4.88 Hz), 7.23 (2H, dd, J=8.55, 5.50 Hz), 7.00 (2H, t, J=8.54 Hz), 4.55 (1H, dd, J=14.95, 6.40 Hz), 4.51 (1H, dd, J=14.95, 6.10 Hz), 3.26 (3H, s), 3.01 (3H, s). HRMS (ESI) calcd for C20H18F2N3O5S (M+H): 450.0935; found: 450.0941.

Workup

customPrepared

Sources & evidence

ORD record: ord-6a218421caf14e148b8064319d15a12a
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07037908B2

Reaction notes

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