Piperazine → HCID 21891291, compound

HRID 720298Notes

Reaction equation

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

Participants

Reactant 2

HCID 4837Piperazine

HCID 21060065HCID 21060065, compound

Product 1

HCID 21891291HCID 21891291, compoundYield 42%

Procedure

Following the procedure described for the synthesis of compound 67A 5-Benzyloxy-2-methanesulfonyl-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (7.0 g, 19.2 mmol) was reacted with piperazine (17.0 g, 192 mmol) and to yield the title compound as a pale yellow oil (0.0418 g, 42% yield). 1H NMR (500 MHz, CDCl3) δ: 7.45 (2H, d, J=6.7 Hz), 7.34–7.27 (3H, m), 5.13 (2H, s), 4.30 (2H, q, J=7.2 Hz), 3.49 (3H, s), 3.15–3.13 (4H, m), 2.98–2.96 (4H, m), 1.89 ( 1H, bs), 1.27 (3H, J=7.2 Hz). HRMS (M+H) calcd for C19H25N4O4: 373.21414. found: 373.1866.

Sources & evidence

ORD record: ord-3b8d4187e87f454f8a9af66dc6f83889
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07135467B2

Reaction notes

Loading…