Triethylamine → HCID 86629459, compound

HRID 599303Notes

Reaction equation

[O:1]=[C:2](Cl)OC(Cl)(Cl)Cl.[Cl:9][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.CCN(CC)CC>>[Cl:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([N+:17]([O-:19])=[O:18])=[CH:12][C:11]=1[N:20]1[CH2:21][C:22]2[CH:27]=[N:26][C:25]([N:28]([O:30][CH3:31])[CH3:29])=[CH:24][C:23]=2[N:32]([CH2:33][CH3:34])[C:2]1=[O:1]

Participants

Reactant 3

HCID 8471Triethylamine

HCID 10426Diphosgene

HCID 86629443HCID 86629443, compound

Product 1

HCID 86629459HCID 86629459, compoundYield 60%

Procedure

Diphosgene (3.1 g, 15.66 mmol), 5-((2-chloro-4-fluoro-5-nitrophenylamino)methyl)-N4-ethyl-N2-methoxy-N2-methylpyridine-2,4-diamine (4.3 g, 13.1 mmol) and Et3N (7 g, 65.2 mmol) were combined by the procedure of Example A4 to give 3-(2-chloro-4-fluoro-5-nitrophenyl)-1-ethyl-7-(methoxy(methyl)amino)-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (2.7 g, 60% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.55 (d, J=7.6 Hz, 1 H), 8.09 (d, J=11.2 Hz, 1 H), 8.00 (s, 1 H), 6.63 (s, 1 H), 4.91 (d, J=13.6 Hz, 1 H), 4.55 (d, J=13.6 Hz, 1 H), 3.93 (m, 2 H), 3.77 (s, 3 H), 3.20 (s, 3 H), 1.23 (t, J=7.2 Hz, 3 H); MS (ESI) m/z: 410.2 [M+H]+.

Sources & evidence

ORD record: ord-8529003a4f8044d4ae4979ae57ed8ba1
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897762B2

Reaction notes

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