2-Bromoethyl methyl ether → HCID 58516003, compound

HRID 717844Notes

Reaction equation

HRID 717844 reaction equation
Cl.[Cl:2][C:3]1[C:4]2[N:5]([CH:18]=[N:19][CH:20]=2)[C:6]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[C:7]([C:9](=[O:11])[CH3:10])[CH:8]=1.C(N(CC)C(C)C)(C)C.Br[CH2:31][CH2:32][O:33][CH3:34]>C(#N)C>[Cl:2][C:3]1[C:4]2[N:5]([CH:18]=[N:19][CH:20]=2)[C:6]([N:12]2[CH2:17][CH2:16][N:15]([CH2:31][CH2:32][O:33][CH3:34])[CH2:14][CH2:13]2)=[C:7]([C:9](=[O:11])[CH3:10])[CH:8]=1

Participants

5

Reactant 3

HCID 809722-Bromoethyl methyl etherHCID 81531DiisopropylethylamineHCID 66992779HCID 66992779, compound

Product 1

HCID 58516003HCID 58516003, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(8-Chloro-5-piperazin-1-ylimidazo[1,5-a]pyridine-6-yl)ethanone hydrochloride (16 mg, 0.052 mmol), N,N-diisopropylethylamine (27 μL, 0.16 mmol) and 1-bromo-2-methoxyethane (4.9 μL, 0.052 mmol) were stirred in acetonitrile (1.0 mL) for 22 hours at 65° C. Purification by preparative LCMS (pH 10) gave the desired compound (10 mg, 60%). LCMS calculated for C16H22ClN4O2 (M+H)+: m/z=337.1. found: 336.9.

Workup

  1. customPurification by preparative LCMS (pH 10)

Sources & evidence

ORD record
ord-71c797e4a81f41e8aa601bfd9972d5b8
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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