1,8-Diazabicyclo(5.4.0)undec-7-ene → tert-butyl 4-(cyanomethyl)-4-{4-[7-(quinolin-6-ylmethyl)imidazo[1,2-b][1,2,4]triazin-2-yl]-1H-pyrazol-1-yl}piperidine-1-carboxylate

HRID 500281Notes

Reaction equation

N12CCCN=C1CCCCC2.[NH:12]1[CH:16]=[C:15]([C:17]2[CH:18]=[N:19][C:20]3[N:21]([C:23]([CH2:26][C:27]4[CH:28]=[C:29]5[C:34](=[CH:35][CH:36]=4)[N:33]=[CH:32][CH:31]=[CH:30]5)=[CH:24][N:25]=3)[N:22]=2)[CH:14]=[N:13]1.[C:37]([CH:39]=[C:40]1[CH2:45][CH2:44][N:43]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:42][CH2:41]1)#[N:38]>C(#N)C>[C:37]([CH2:39][C:40]1([N:12]2[CH:16]=[C:15]([C:17]3[CH:18]=[N:19][C:20]4[N:21]([C:23]([CH2:26][C:27]5[CH:28]=[C:29]6[C:34](=[CH:35][CH:36]=5)[N:33]=[CH:32][CH:31]=[CH:30]6)=[CH:24][N:25]=4)[N:22]=3)[CH:14]=[N:13]2)[CH2:41][CH2:42][N:43]([C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:44][CH2:45]1)#[N:38]

Participants

Conditions

Temperature: 60 °C

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (68 μL, 0.46 mmol) was added to a mixture of 6-[2-(1H-pyrazol-4-yl)imidazo[1,2-b][1,2,4]triazin-7-yl]methylquinoline (50.0 mg, 0.153 mmol) and tert-butyl 4-(cyanomethylene)piperidine-1-carboxylate (0.068 g, 0.30 mmol) in acetonitrile (1 mL). The reaction was stirred at 60° C. overnight. After cooling to RT, the mixture was purified by chromatography on silica gel with EtOAc in CH2Cl2 (0-70%) to give the desired product (30 mg, 35.7%). LCMS: (M+H)=550.5.

Workup

temperatureAfter cooling to RT
customthe mixture was purified by chromatography on silica gel with EtOAc in CH2Cl2 (0-70%)

Sources & evidence

ORD record: ord-f867e6d1b77c44538b5b019d27258262
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767675B2

Reaction notes

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