Triethylamine → HCID 86629442, compound

HRID 599284Notes

Reaction equation

O=C(Cl)[O:3][C:4](Cl)(Cl)Cl.Cl[C:10]1[CH:15]=[C:14]([F:16])[C:13]([N+:17]([O-:19])=[O:18])=[CH:12][C:11]=1[NH:20][CH2:21][C:22]1[C:23]([NH:32][CH2:33][CH3:34])=[CH:24][C:25]([N:28]([O:30][CH3:31])[CH3:29])=[N:26][CH:27]=1.[CH3:35]CN(CC)CC>>[CH2:33]([N:32]1[C:23]2[CH:24]=[C:25]([N:28]([O:30][CH3:31])[CH3:29])[N:26]=[CH:27][C:22]=2[CH2:21][N:20]([C:11]2[CH:12]=[C:13]([N+:17]([O-:19])=[O:18])[C:14]([F:16])=[CH:15][C:10]=2[CH3:35])[C:4]1=[O:3])[CH3:34]

Participants

Reactant 3

HCID 8471Triethylamine

HCID 10426Diphosgene

HCID 86629443HCID 86629443, compound

Product 1

HCID 86629442HCID 86629442, compoundYield 72.2%

Procedure

Diphosgene (2.4 mL, 19 mmol), 5-((2-chloro-4-fluoro-5-nitrophenylamino)methyl)-N4-ethyl-N2-methoxy-N2-methylpyridine-2,4-diamine (6 g, 16 mmol) and Et3N (4.6 mL, 32 mmol) were combined by the procedure of Example A4 step 3 to provide 1-ethyl-3-(4-fluoro-2-methyl-5-nitro-phenyl)-7-(methoxy(methyl)amino)-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (4.5 g, 70% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.27 (d, J=8 Hz, 1 H), 7.94 (s, 1 H), 7.58 (d, J=12 Hz, 1 H), 6.58 (s, 1 H), 4.89 (d, J=16 Hz, 1 H), 4.48 (d, J=16 Hz, 1 H), 3.84-3.92 (m, 2H), 3.73 (s, 3 H), 3.16 (s, 3 H), 2.20 (s, 1 H), 1.19 (t, J=8 Hz, 3 H); MS (ESI) m/z: 390.2 [M+H]+.

Sources & evidence

ORD record: ord-d1baef5289c74e7d9ba7ccf86d822312
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897762B2

Reaction notes

Loading…