(1H-indol-5-yl)methanamine → HCID 25061100, compound

HRID 657819Notes

Reaction equation

HRID 657819 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.[NH:21]1[C:29]2[C:24](=[CH:25][C:26](CN)=[CH:27][CH:28]=2)[CH:23]=[CH:22]1.[CH:32]([N:35](CC)C(C)C)(C)C>C(#N)C>[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([CH2:32][NH:35][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:28]=2)[CH:23]=[CH:22]1

Participants

5

Reactant 3

HCID 54791(1H-indol-5-yl)methanamineHCID 81531DiisopropylethylamineHCID 598406882-(4-Chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile

Product 1

HCID 25061100HCID 25061100, compound

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 (100 mg, 0.35 mmol) and 1-(1H-indol-5-yl)-methylamine (139 mg, 0.95 mmol) in acetonitrile (1 mL) and N,N-diisopropylethylamine (0.4 mL, 2 mmol) was subjected to microwave irradiation at 185° C. for 3 h. The reaction mixture was concentrated and the residue was purified by preparative HPLC (30-60% acetonitrile-water [10 mM DEA]) 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 (30-60% acetonitrile-water [10 mM DEA])
  4. customto afford a light yellow solid

Sources & evidence

ORD record
ord-d5372a14abb04deea37aa9405eb48b6f
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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