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Triethylamine → HCID 53358060, compound

HRID 1500775
Notes
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Reaction equation

HRID 1500775 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 67327163HCID 67327163, compound

Product 1

HCID 53358060HCID 53358060, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

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

  1. temperatureThe reaction mixture was then cooled to ambient temperature
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes