Dipropylamine → HCID 9865741, compound

HRID 2299270Notes

Reaction equation

Cl[C:2]1[C:14]2[N:9]3[CH:10]=[CH:11][N:12]=[CH:13][C:8]3=[C:7]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:6]=2[N:5]=[C:4]([CH3:24])[CH:3]=1.[CH2:25]([NH:28][CH2:29][CH2:30][CH3:31])[CH2:26][CH3:27]>CS(C)=O.[Cl-].[NH4+]>[CH2:25]([N:28]([C:2]1[C:14]2[N:9]3[CH:10]=[CH:11][N:12]=[CH:13][C:8]3=[C:7]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:6]=2[N:5]=[C:4]([CH3:24])[CH:3]=1)[CH2:29][CH2:30][CH3:31])[CH2:26][CH3:27]

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 4-Chloro-2-methyl-10-(2,4,6-trimethylphenyl)pyrido-[2′,3′:4,5]pyrrolo[1,2-a]pyrazine (23 mg) in DMSO (0.5 mL) is added dipropylamine (0.1 mL) and the resulting mixture is heated at 130° C. for 3.5 days. The mixture is then allowed to cool to room temperature, diluted with aqueous ammonium chloride, and extracted twice with ethyl ether. The extracts are combined, washed with saturated brine, dried (Na2SO4), filtered, concentrated in vacuo, and chromatographed (10 to 20% ethyl acetate in hexane) to give 14.3 mg of the title compound (compound 6, Table 1) as a yellow, glassy oil: 0.90 (t, 6 H), 1.6 (m, 4 H), 2.03 (s, 6 H), 2.38 (s, 3 H), 2.62 (s, 3 H), 3.2 (br, 4 H), 6.81 (s, 1 H), 7.02 (s, 2 H), 7.60 (d, 2 H), 8.6 (m, 2 H).

Workup

temperatureto cool to room temperature
extractionextracted twice with ethyl ether
washwashed with saturated brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customchromatographed (10 to 20% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-6a082836ace84633bda23e88c07abefe
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06495686B2

Reaction notes

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