1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 53497452, compound

HRID 1852976Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[N:15][NH:16][CH:17]=3)[N:10]3[CH:18]=[CH:19][N:20]=[C:9]3[CH:8]=2)[CH:4]=[N:3]1.C[C:22](C)(C)[CH2:23][CH:24]=[CH:25][C:26]#[N:27].[N:30]1CCCN2CCCCCC=12>CN(C)C=O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[N:15][N:16]([CH:24]([CH2:23][C:22]#[N:30])[CH2:25][C:26]#[N:27])[CH:17]=3)[N:10]3[CH:18]=[CH:19][N:20]=[C:9]3[CH:8]=2)[CH:4]=[N:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

7-(1-Methyl-1H-pyrazol-4-yl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (Preparation K; 0.040 mg, 0.15 mmol) was dissolved in dimethylformamide (0.6 mL) and 5,5-dimethylhex-2-enenitrile (Table 1, compound k; 56 mg, 0.045 mmol) and 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (34 mg, 0.23 mmol) were added and the reaction was heated at 50° C. for 7 hours. The reaction was then cooled and the solvent was removed. The crude reaction was purified by silica gel chromatography using a gradient (1 to 4% MeOH/DCM) to provide 3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)pentanedinitrile (37 mg, 63% yield) as a solid. MS (apci) m/z=389.2 (M+H).

Workup

temperatureThe reaction was then cooled
customthe solvent was removed
customThe crude reaction
customwas purified by silica gel chromatography

Sources & evidence

ORD record: ord-b2a679d4f3c8483197ccba5bbd72b913
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962596B2

Reaction notes

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