1-(4-Chloro-3-(methylsulfonyl)phenyl)ethanamine → 2-(4-(1-(4-chloro-3-(methylsulfonyl)phenyl)ethylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile

HRID 657824Notes

Reaction equation

HRID 657824 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.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([NH2:30])[CH3:29])=[CH:24][C:23]=1[S:31]([CH3:34])(=[O:33])=[O:32]>C(#N)C.C(N(CC)C(C)C)(C)C>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([NH:30][C:2]2[C:3]3[CH2:11][N:10]([C:12]4[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:13]=4[C:14]#[N:15])[CH2:9][CH2:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH3:29])=[CH:24][C:23]=1[S:31]([CH3:34])(=[O:32])=[O:33]

Participants

5

Reactant 2

HCID 581881711-(4-Chloro-3-(methylsulfonyl)phenyl)ethanamineHCID 598406882-(4-Chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile

Product 1

HCID 250613602-(4-(1-(4-chloro-3-(methylsulfonyl)phenyl)ethylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A reaction mixture of 2-(4-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile (250 mg, 0.88 mmol) and 1-(4-chloro-3-(methylsulfonyl)phenyl)ethanamine (300 mg, 1.28 mmol) in acetonitrile (2 mL) and N,N-diisopropylethylamine (700 μL) 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 yellow solid.

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])
  4. customto afford a light yellow solid

Sources & evidence

ORD record
ord-71236bf522e8407295a18c0113e6bf02
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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