Triethylamine → HCID 86629438, compound

HRID 599281Notes

Reaction equation

HRID 599281 reaction equation
O=C(Cl)[O:3][C:4](Cl)(Cl)Cl.[F:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]([NH:19][CH2:20][C:21]2[C:22]([NH:31][CH:32]([CH3:34])[CH3:33])=[CH:23][C:24]([N:27]([O:29][CH3:30])[CH3:28])=[N:25][CH:26]=2)=[C:12]([CH3:35])[CH:11]=1.CCN(CC)CC>O1CCOCC1>[F:9][C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]([N:19]2[CH2:20][C:21]3[CH:26]=[N:25][C:24]([N:27]([O:29][CH3:30])[CH3:28])=[CH:23][C:22]=3[N:31]([CH:32]([CH3:33])[CH3:34])[C:4]2=[O:3])=[C:12]([CH3:35])[CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 86629439HCID 86629439, compound

Product 1

HCID 86629438HCID 86629438, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Using the procedure of Example A4 step 3, diphosgene (1.3 g, 6.4 mmol), 5-((4-fluoro-2-methyl-5-nitrophenylamino)methyl)-N4-isopropyl-N2-methoxy-N2-methylpyridine-2,4-diamine (2.0 g, 5.3 mmol) and Et3N (2.2 g, 21.2 mmol) were reacted in dioxane to give 3-(4-fluoro-2-methyl-5-nitrophenyl)-1-isopropyl-7-(methoxy(methyl)amino)-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (1.5 g, 70% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.18 (d, J=7.2 Hz, 1 H), 7.94 (s, 1 H), 7.55 (d, J=12.4 Hz, 1 H), 6.68 (s, 1 H), 4.77 (d, J=13.6 Hz, 1 H), 4.45-4.37 (m, 2 H), 3.71 (s, 3 H), 3.13 (s, 3 H), 2.14 (s, 3 H), 1.46 (t, J=6.4 Hz, 6H).

Sources & evidence

ORD record
ord-67011e91f385424ba663ff4b732b4de3
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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