HCID 178476588, compound → HCID 178476590, compound

HRID 245670Notes

Reaction equation

HRID 245670 reaction equation
[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11](=O)[NH:12][CH2:13][C:14]2[C:19](Cl)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[C:22](O[C@H]1CC[C@H](C2N3C=CN=C(Cl)C3=CN=2)CC1)(=O)C>>[C:1]([O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([CH3:22])[C:14]3=[CH:13][N:12]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 178476588HCID 178476588, compoundHCID 178476598HCID 178476598, compound

Product 1

HCID 178476590HCID 178476590, compoundYield 78.2%

Procedure

(Trans)-4-((3-chloropyrazin-2-yl)methylcarbamoyl)cyclohexyl acetate (2.8 g) was transformed into (trans)-4-(8-chloroimidazo[1,5-a]pyrazin-3-yl)cyclohexyl acetate (2.2 g) using the procedure described in example 1 step 1b using a reaction temperature of 60° C. for 16 hours. Reaction of the latter compound (2.6 g) yielded (trans)-4-(8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl acetate (1.6 g) using the procedure described in example 2 step 2d.

Workup

  1. customa reaction temperature of 60° C.
  2. customfor 16 hours

Sources & evidence

ORD record
ord-116332168e744e738c46f56f9d620103
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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