3-Pentanol → HCID 58045968, compound

HRID 657891Notes

Reaction equation

[H-].[Na+].Br.Cl[C:5]1[C:6]2[CH2:17][CH2:16][CH2:15][C:7]=2[C:8]2[N:9]([C:11]([NH2:14])=[N:12][N:13]=2)[N:10]=1.[CH3:18][CH2:19][CH:20]([OH:23])[CH2:21][CH3:22]>CN(C=O)C>[CH2:19]([CH:20]([O:23][C:5]1[C:6]2[CH2:17][CH2:16][CH2:15][C:7]=2[C:8]2[N:9]([C:11]([NH2:14])=[N:12][N:13]=2)[N:10]=1)[CH2:21][CH3:22])[CH3:18]

Participants

Conditions

Temperature: 50 °C

Procedure

3-Pentanol (20 ml) was initially charged under argon, admixed with sodium hydride (991 mg) and stirred at 50° C. for 1 h. Subsequently, 6-chloro-8,9-dihydro-7H-cyclopenta[d][1,2,4]-triazolo[4,3-b]pyridazin-3-ylamine hydrobromide (W2.017, 2.0 g), dissolved in 3-pentanol (20 ml) and DMF (100 ml), was slowly added dropwise within 1 h. After stirring for 1 h, the mixture was concentrated, and the residue was admixed with water and extracted four times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified using a 40 g silica gel cartridge (dichloromethane-methanol gradient 0-10% in 50 min). The clean product fractions were combined and dried. 1.04 g of the title compound were obtained.

Workup

stirringAfter stirring for 1 h
concentrationthe mixture was concentrated
extractionextracted four times with dichloromethane
dry with materialThe combined organic phases were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified
customa 40 g silica gel cartridge (dichloromethane-methanol gradient 0-10% in 50 min)
customdried

Sources & evidence

ORD record: ord-4c7d4aacec67422e9123a5762639b796
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076336B2

Reaction notes

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