Triethylamine → HCID 66802288, compound

HRID 528044Notes

Reaction equation

HRID 528044 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:12]1[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=1)[N:6]2[CH3:11].[N:18]1([C:24]2[CH:25]=[C:26]([CH:37]=[CH:38][CH:39]=2)[O:27][CH2:28][C:29]([N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[O:30])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(N(CC)CC)C>C(O)(C)C>[CH3:11][N:6]1[C:5]([C:12]2[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=2)=[N:4][C:3]2[C:7]1=[N:8][CH:9]=[N:10][C:2]=2[N:21]1[CH2:22][CH2:23][N:18]([C:24]2[CH:39]=[CH:38][CH:37]=[C:26]([O:27][CH2:28][C:29](=[O:30])[N:31]3[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]3)[CH:25]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66806517HCID 66806517, compoundHCID 86711714HCID 86711714, compound

Product 1

HCID 66802288HCID 66802288, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A stirred solution of 6-chloro-9-methyl-8-(1-methyl-1H-pyrazol-4-yl)-9H-purine (30 mg, 0.12 mmol), 2-(3-(piperazin-1-yl)phenoxy)-1-(piperidin-1-yl)ethanone (45.5 mg, 0.15 mmol), and triethylamine (84.0 uL, 0.60 mmol) in isopropyl alcohol (2.0 mL) were heated to 80° C. for 16 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The product was purified by preparatory HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid) to give 6.1 mg (10% yield) of the title compound. 1H NMR (400 MHz, DMSO-d6): δ 8.44 (s, 1H), 8.27-8.25 (m, 1H), 8.05 (s, 1H), 7.12 (t, 1H), 6.62 (dd, 1H), 6.55 (t, 1H), 6.39-6.35 (m, 1H), 4.73 (s, 2H), 3.96 (s, 3H), 3.85 (s, 3H), 3.46-3.37 (m, 4H), 3.30-3.24 (m, 6H), 3.17 (d, 2H), 1.63-1.48 (m, 4H), 1.43 (s, 2H). MS (EI) for C27H33N9O2: 516.7 (MH+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe product was purified by preparatory HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid)

Sources & evidence

ORD record
ord-463a8423ac7b408a885915d8863e1f8b
Source dataset
uspto-grants-2016_05
Patent number
US09346807B2

Reaction notes

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