Methanol → HCID 20626966, compound

HRID 270725Notes

Reaction equation

[F:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[C:20](=[O:21])[N:19]([CH3:22])[C:10]3[N:11]=[C:12](S(C)(=O)=O)[N:13]=[CH:14][C:9]=3[CH:8]=2)=[CH:4][CH:3]=1.[CH2:25]([N:27]([CH2:38][CH3:39])[CH2:28][CH2:29][O:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1)[CH3:26].CO>CN1CCCC1=O>[CH2:38]([N:27]([CH2:25][CH3:26])[CH2:28][CH2:29][O:30][C:31]1[CH:32]=[CH:33][C:34]([NH:35][C:12]2[N:13]=[CH:14][C:9]3[CH:8]=[C:7]([O:6][C:5]4[CH:23]=[CH:24][C:2]([F:1])=[CH:3][CH:4]=4)[C:20](=[O:21])[N:19]([CH3:22])[C:10]=3[N:11]=2)=[CH:36][CH:37]=1)[CH3:39]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 6-(4-fluorophenoxy)-8-methyl-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one (see Example 8-Step A-B, 0.35 g, 1 mmol) and 4-(2-diethylaminoethoxy)aniline (0.625 g, 3 mmol) in 0.5 mL 1-methyl-2-pyrrolidinone was stirred at 110° C. for 12 hours and then cooled to room temperature. Methanol (2 mL) was added and the suspension was stirred for 30 minutes. Filtration and washing of the precipitate thoroughly with methanol followed by drying provided the free amine. This was suspended in ethyl acetate (1-2 mL), hydrochloric acid in ether (1M, 1.2 eq) was added and the reaction was stirred for 30 minutes. Isolation of the solid via filtration and drying provided 0.085 g of the hydrochloride salt (Mass spec. M+1=478, MP=245.2-246.1° C.).

Workup

temperaturecooled to room temperature
stirringthe suspension was stirred for 30 minutes
filtrationFiltration
washwashing of the precipitate thoroughly with methanol
customby drying

Sources & evidence

ORD record: ord-fc4b199906df409a9421e56e115b7a77
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449581B2

Reaction notes

Loading…