Tris(hydroxymethyl)aminomethane → Propanamide, N-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2-methyl-

HRID 68662Notes

Reaction equation

HRID 68662 reaction equation
[CH3:1][CH:2]([CH3:6])[C:3](O)=[O:4].C(Cl)(=O)C(Cl)=O.[Br:13][C:14]1[N:15]=[C:16]2[C:22]([NH2:23])=[CH:21][NH:20][C:17]2=[N:18][CH:19]=1.C(O)C(N)(CO)CO.C(=O)([O-])[O-]>O1CCOCC1.CN(C=O)C>[Br:13][C:14]1[N:15]=[C:16]2[C:22]([NH:23][C:3](=[O:4])[CH:2]([CH3:6])[CH3:1])=[CH:21][NH:20][C:17]2=[N:18][CH:19]=1

Participants

8

Reactant 5

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 6590Isobutyric AcidHCID 19660Carbonate IonHCID 65578Oxalyl chlorideHCID 86675703HCID 86675703, compound

Product 1

HCID 86675705Propanamide, N-(2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2-methyl-

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-methyl propanoic acid (62.06 mg, 65.46 μL, 0.7044 mmol) in dioxane (1 mL) with DMF was added oxalyl chloride (87.9 mg, 60.43 μL, 0.6927 mmol) at ambient temperature. The resulting solution was stirred for 30 minutes at this temperature. To this solution was added 2-bromo-5H-pyrrolo[2,3-b]pyrazin-7-amine (50 mg, 0.2347 mmol) and this was stirred for a further 4 hours at ambient temperature. The reaction mixture was then heated to 50° C. for 1 hour. After this time trisamine resin and carbonate resin were added and the sample filtered. This crude solution was taken onto the next step as is.

Workup

  1. stirringthis was stirred for a further 4 hours at ambient temperature
  2. filtrationthe sample filtered

Sources & evidence

ORD record
ord-2fc3d6edb451482b881db0ed87eef2ab
Source dataset
uspto-grants-2014_09
Patent number
US08822469B2

Reaction notes

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