1,1'-Carbonyldiimidazole → HCID 136373231, compound

HRID 388146Notes

Reaction equation

HRID 388146 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][N:14]3[CH3:19])[C:9](=[O:11])[NH:10][C:5]2=[N:4][CH:3]=1.BrC1N=C(N[CH2:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31]N2C)C(N)=NC=1.C(N1C=CN=C1)(N1C=CN=C1)=[O:38]>O1CCCC1>[OH:38][C:29]1[CH:34]=[CH:33][C:32]([C:2]2[N:7]=[C:6]3[N:8]([CH2:12][CH:13]4[CH2:18][CH2:17][CH2:16][CH2:15][N:14]4[CH3:19])[C:9](=[O:11])[NH:10][C:5]3=[N:4][CH:3]=2)=[CH:31][CH:28]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 86626417HCID 86626417, compoundHCID 86626418HCID 86626418, compound

Product 1

HCID 136373231HCID 136373231, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Bromo-1-((1-methylpiperidin-2-yl)methyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one. A solution of 6-bromo-N2-((1-methylpiperidin-2-yl)methyl)pyrazine-2,3-diamine (0.48 g, 1.599 mmol) and 1,1′-carbonyldiimidazole (0.324 g, 1.999 mmol) in anhydrous tetrahydrofuran (15 mL) was heated overnight at 115° C. The volatiles were removed under reduced pressure, and the crude product was purified by Biotage column chromatography (0-15% methanol in dichloromethane) to provide the title compound (0.48 g, 1.472 mmol, 92% yield). MS (ESI) m/z 327.2 [M+1]+.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe crude product was purified by Biotage column chromatography (0-15% methanol in dichloromethane)

Sources & evidence

ORD record
ord-0f6929594d50402da6892ec6a503feeb
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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