4-Fluorobenzylamine → HCID 54682043, compound

HRID 720300Notes

Reaction equation

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

Participants

Reactant 2

HCID 673264-Fluorobenzylamine

HCID 58739059HCID 58739059, compound

Product 1

HCID 54682043HCID 54682043, compound

Procedure

N-[(4-fluorophenyl)methyl]-1,6-dihydro-5-hydroxy-1-methyl-2-[4-(methylsulfonyl)-1-piperazinyl]-6-oxo-4-pyrimidinecarboxamide was synthesized from 5-hydroxy-2-(4-methanesulfonyl-piperazin-1-yl)-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester and 4-fluorobenzylamine as described in example to yield the title compound as a white solid 1H NMR (300 MHz, MeOD) δ: 8.88 (1H, t, J=5.9 Hz), 7.37 (2H, dd, J=8.6, 5.3 Hz), 7.05 (2H, t, J=8.8 Hz), 4.55 (2H, d, J=6.2 Hz), 3.55 (3H, s), 3.39–3.36 (4H, m), 3.26–3.23 (4H, m), 2.88 (3H, s). HRMS (M+H) calcd for C18H23FN5O5S: 440.14040. found: 440.1386.

Sources & evidence

ORD record: ord-4f409ab7b72f4c36b2d75dcae5da160d
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07135467B2

Reaction notes

Loading…