Triethylamine → 6-(9-((5-chloro-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)nicotinonitrile

HRID 1478035Notes

Reaction equation

HRID 1478035 reaction equation
[Cl:1][C:2]1[C:3]([NH:15][CH:16]2[CH2:26][CH2:25][C:19]3([CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH2:18][CH2:17]2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=1.Cl[C:28]1[N:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=1.CCN(CC)CC>C(Cl)Cl.CO>[Cl:1][C:2]1[C:3]([NH:15][CH:16]2[CH2:26][CH2:25][C:19]3([CH2:24][CH2:23][N:22]([C:28]4[CH:29]=[CH:30][C:31]([C:34]#[N:35])=[CH:32][N:33]=4)[CH2:21][CH2:20]3)[CH2:18][CH2:17]2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 1183900695-chloro-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(3-azaspiro[5.5]undecan-9-yl) pyrimidine-2,4-diamine

Product 1

HCID 1183900256-(9-((5-chloro-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)nicotinonitrileYield 39.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-chloro-N2-(1-methyl-1H-pyrazol-4-yl)-N4-(3-azaspiro[5.5]undecan-9-yl) pyrimidine-2,4-diamine (0.11 g, 0.29 mmol) in a mixture of DCM and MeOH (5.0 mL/5.0 mL) were added 6-chloropyridine-3-carbonitrile (0.086 g, 0.62 mmol) and Et3N (0.10 mL, 0.72 mmol). The mixture was heated to reflux overnight and then concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=50/1) to afford the product as a light yellow solid (55 mg, 39%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=50/1)

Sources & evidence

ORD record
ord-4088088784e24c08a01e50de2a7afb52
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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