Triethylamine → HCID 53358060, compound

HRID 1500775Notes

Reaction equation

Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][N:3]=1.C(N(CC)CC)C.[NH:17]1[CH2:22][CH2:21][CH2:20][C@@H:19]([NH:23][C:24]2[CH:29]=[CH:28][N:27]=[C:26]([C:30]3[CH:31]=[N:32][N:33]4[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][C:34]=34)[N:25]=2)[CH2:18]1.C(=O)([O-])O.[Na+]>ClCCl>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([N:17]2[CH2:22][CH2:21][CH2:20][C@@H:19]([NH:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]([C:30]4[CH:31]=[N:32][N:33]5[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][C:34]=45)[N:25]=3)[CH2:18]2)=[N:3][CH:4]=1)#[N:7]

Participants

Conditions

Temperature: 50 °C

Procedure

6-Chloronicotinonitrile (0.04 g, 0.29 mmol) and triethylamine (0.15 mL, 1.08 mmol) were added to a stirred solution of 3-{4-[(3R)-piperidin-3-ylamino]pyrimidin-2-yl}pyrazolo[1,5-a]pyridine-5-carbonitrile (Preparation 7b, 0.11 g, 0.24 mmol) in dichloromethane (3.3 mL) and the resulting mixture was stirred at 50° C. for 20 hours. The reaction mixture was then cooled to ambient temperature and dichloromethane and 4% aqueous sodium hydrogencarbonate solution were added. The organic layer was separated, washed with water and brine, dried (MgSO4) and evaporated in vacuo. The crude product was purified by flash chromatography (200:1 to 60:1 chloroform/methanol) to give the title compound (0.07 g, 71%) as a pale yellow solid.

Workup

temperatureThe reaction mixture was then cooled to ambient temperature
customThe organic layer was separated
washwashed with water and brine
dry with materialdried (MgSO4)
customevaporated in vacuo
customThe crude product was purified by flash chromatography (200:1 to 60:1 chloroform/methanol)

Sources & evidence

ORD record: ord-ae21d8d747f84bdfb822994bcb910138
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206183B2

Reaction notes

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