Triethylamine → HCID 66802080, compound

HRID 528046Notes

Reaction equation

HRID 528046 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].[CH3:18][C:19]1[CH:20]=[C:21]([CH:38]=[CH:39][CH:40]=1)[C:22]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1)=[O:23].C(N(CC)CC)C>C(O)(C)C>[CH3:18][C:19]1[CH:20]=[C:21]([CH:38]=[CH:39][CH:40]=1)[C:22]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[CH2:33][CH2:34][N:35]([C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[C:5]([C:12]2[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=2)[N:6]3[CH3:11])[CH2:36][CH2:37]1)=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66799845HCID 66799845, compoundHCID 86711714HCID 86711714, compound

Product 1

HCID 66802080HCID 66802080, compoundYield 50.3%

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), 3-methyl-N-(2-(piperazin-1-yl)benzyl)benzamide (46.4 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 31.5 mg (50% 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-b8053f1cf6ea46b29c7d88fed2dd443e
Source dataset
uspto-grants-2016_05
Patent number
US09346807B2

Reaction notes

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