Triethylamine → HCID 71509280, compound

HRID 868818Notes

Reaction equation

HRID 868818 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([O:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[C:12]([CH:15]=2)[C:13]#[N:14])[CH:5]=[CH:4][N:3]=1.O1CCOCC1.[CH3:29][O:30][CH2:31][CH2:32][CH2:33][N:34]1[CH:38]=[C:37]([NH2:39])[CH:36]=[N:35]1.C(N(CC)CC)C>C(O)C>[CH3:29][O:30][CH2:31][CH2:32][CH2:33][N:34]1[CH:38]=[C:37]([NH:39][C:2]2[N:7]=[C:6]([C:8]3[CH:9]=[CH:10][C:11]([O:16][CH:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[C:12]([CH:15]=3)[C:13]#[N:14])[CH:5]=[CH:4][N:3]=2)[CH:36]=[N:35]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 60925752HCID 60925752, compoundHCID 866710095-(2-Chloro-4-pyrimidinyl)-2-[(tetrahydro-2H-pyran-4-yl)oxy]benzonitrile

Product 1

HCID 71509280HCID 71509280, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

5-(2-Chloropyrimidin-4-yl)-2-(tetrahydropyran-4-yloxy)benzonitrile (200 mg) are dissolved in ethanol and dioxane in a 100 ml three-necked flask, and the 1-(3-methoxypropyl)-1H-pyrazol-4-ylamine (129 mg) prepared above and 0.8 ml of triethylamine are added. The yellow solution is stirred at 100° C. for two days. For work-up, the mixture is evaporated in a rotary evaporator and purified by chromatography, giving 71 mg of the desired product; HPLC-MS Rt. [min] 2.041; HPLC-MS [M+H] 435;

Workup

  1. additionare added
  2. customFor work-up, the mixture is evaporated in a rotary evaporator
  3. custompurified by chromatography

Sources & evidence

ORD record
ord-cbe8ecb6dd4e42efa111250281941df3
Source dataset
uspto-grants-2015_03
Patent number
US08969335B2

Reaction notes

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