1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86685335, compound

HRID 1853068Notes

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.[CH2:21]1[C:24]2([CH2:27][C:26](=[CH:28][C:29]#[N:30])[CH2:25]2)[CH2:23][O:22]1.C1CCN2C(=NCCC2)CC1>C(#N)C>[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]([C:26]4([CH2:28][C:29]#[N:30])[CH2:27][C:24]5([CH2:23][O:22][CH2:21]5)[CH2:25]4)[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

A mixture of 7-(1-methyl-1H-pyrazol-4-yl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (25 mg; 0.094 mmol), 2-(2-oxaspiro[3.3]heptan-6-ylidene)acetonitrile (19 mg; 0.14 mmol) and DBU (7.2 mg; 0.047 mmol) in acetonitrile (1 mL) was stirred in a sealed vial at 50° C. for 24 hours. The solvent was removed under reduced pressure and the material was purified by silica gel chromatography, eluting with (6% ammonium hydroxide in methanol)/methylene chloride (1:25 to 1:15 gradient) to provide pure desired product as a white solid (27.5 mg). MS (apci) m/z=401.1 (M+H).

Workup

customThe solvent was removed under reduced pressure
customthe material was purified by silica gel chromatography
washeluting with (6% ammonium hydroxide in methanol)/methylene chloride (1:25 to 1:15 gradient)

Sources & evidence

ORD record: ord-0567521aee084b7d906dd9ce3fd8e965
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962596B2

Reaction notes

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