Methanol → 2,2-Dimethyl-1-[2-(3-piperidin-1-ylmethyl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one

HRID 1677454Notes

Reaction equation

HRID 1677454 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.Cl.[N:18]1([CH2:24][C:25]2[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[NH4+].[OH-].CO>C(Cl)Cl>[CH3:13][C:12]([CH3:15])([CH3:14])[C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:27]3[CH:28]=[CH:29][CH:30]=[C:25]([CH2:24][N:18]4[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]4)[CH:26]=3)[N:3]=2)[NH:8][CH:9]=1)=[O:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 46738812(3-(Piperidin-1-ylmethyl)phenyl)boronic acid hydrochlorideHCID 578292181-(2-Bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one

Product 1

HCID 595410322,2-Dimethyl-1-[2-(3-piperidin-1-ylmethyl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2-Dimethyl-1-[2-(3-piperidin-1-ylmethyl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one was prepared starting from 1-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one and 3-(piperidin-1-ylmethyl)phenylboronic acid hydrochloride following general procedures as described in these Examples. Silica gel chromatography using 0-20% [5% NH4OH:MeOH]/DCM as eluant gave a brown solid which was washed with 1:2 Et2O/Hexanes to provide 70 mg (36%) of a pale brown solid. MP 176-177° C., M+H=377.

Workup

  1. customgave a brown solid which
  2. washwas washed with 1:2 Et2O/Hexanes

Sources & evidence

ORD record
ord-45c8d0c7992846f390917a8915adb878
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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