Diisopropylethylamine → HCID 25061105, compound

HRID 657825Notes

Reaction equation

HRID 657825 reaction equation
Cl[C:2]1[C:3]2[CH2:11][N:10]([C:12]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:13]=3[C:14]#[N:15])[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[N:21]1[C:30]2[C:25](=[CH:26][C:27]([CH:31]([NH2:33])[CH3:32])=[CH:28][CH:29]=2)[N:24]=[CH:23][CH:22]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:20][C:17]1[CH:18]=[CH:19][C:12]([N:10]2[CH2:9][CH2:8][C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH:33][CH:31]([C:27]4[CH:26]=[C:25]5[C:30](=[CH:29][CH:28]=4)[N:21]=[CH:22][CH:23]=[N:24]5)[CH3:32])[C:3]=3[CH2:11]2)=[C:13]([CH:16]=1)[C:14]#[N:15]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 49761711HCID 49761711, compoundHCID 598406882-(4-Chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile

Product 1

HCID 25061105HCID 25061105, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A reaction mixture of 2-(4-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile (200 mg, 0.70 mmol) and 1-(quinoxalin-6-yl)ethanamine (150 mg, 0.87 mmol) in acetonitrile (2 mL) and N,N-diisopropylethylamine (734 μL, 4.2 mmol) was subjected to microwave irradiation at 185° C. for 3.5 h. The reaction mixture was concentrated and the residue was purified by preparative HPLC (100×20.2 mm, C18 column; 30-60% acetonitrile-water [10 mM Et2NH]) to afford a light brown solid (45 mg).

Workup

  1. customirradiation at 185° C. for 3.5 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by preparative HPLC (100×20.2 mm, C18 column; 30-60% acetonitrile-water [10 mM Et2NH])

Sources & evidence

ORD record
ord-cdaa20bf08314291821ab1d08974a4f6
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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