Triethylamine → HCID 56948811, compound

HRID 528045Notes

Reaction equation

HRID 528045 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].[CH:18]1([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[CH:25][CH:24]=2)[CH2:20][CH2:19]1.C(N(CC)CC)C>C(O)(C)C>[CH:18]1([CH2:21][O:22][C:23]2[CH:24]=[CH:25][C:26]([N:29]3[CH2:34][CH2:33][N:32]([C:2]4[N:10]=[CH:9][N:8]=[C:7]5[C:3]=4[N:4]=[C:5]([C:12]4[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=4)[N:6]5[CH3:11])[CH2:31][CH2:30]3)=[CH:27][CH:28]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21363824HCID 21363824, compoundHCID 86711714HCID 86711714, compound

Product 1

HCID 56948811HCID 56948811, compoundYield 30.2%

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), 1-(4-(cyclopropylmethoxy)phenyl)piperazine (34.8 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 16.1 mg (30% yield) of the title compound.

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-57fc7cee19274d999069f761d1a914b3
Source dataset
uspto-grants-2016_05
Patent number
US09346807B2

Reaction notes

Loading…