Benzo-1,3-dioxole-5-methylamine → HCID 25061101, compound

HRID 657820Notes

Reaction equation

HRID 657820 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.[CH2:21]([NH2:31])[C:22]1[CH:30]=[CH:29][C:28]2[O:27][CH2:26][O:25][C:24]=2[CH:23]=1>C(#N)C.C(N(CC)C(C)C)(C)C>[O:27]1[C:28]2[CH:29]=[CH:30][C:22]([CH2:21][NH:31][C:2]3[C:3]4[CH2:11][N:10]([C:12]5[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:13]=5[C:14]#[N:15])[CH2:9][CH2:8][C:4]=4[N:5]=[CH:6][N:7]=3)=[CH:23][C:24]=2[O:25][CH2:26]1

Participants

5

Reactant 2

HCID 75799Benzo-1,3-dioxole-5-methylamineHCID 598406882-(4-Chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile

Product 1

HCID 25061101HCID 25061101, compound

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 (100 mg, 0.35 mmol) and piperonylamine (120 mg, 0.79 mmol) in acetonitrile (1 mL) and N,N-diisopropylethylamine (400 μL) was subjected to microwave irradiation at 185° C. for 3 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 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-105407fc307a4e6097f779a4a45f6ab6
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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