Trifluoroacetic acid → HCID 58382287, compound

HRID 1628046Notes

Reaction equation

HRID 1628046 reaction equation
[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:33](COCC[Si](C)(C)C)[C:16]4=[N:17][CH:18]=[C:19]([N:21]([CH2:29][C:30](=O)[CH3:31])C(=O)OC(C)(C)C)[N:20]=[C:15]4[CH:14]=3)=[CH:9][CH:8]=2)OCC[O:3]1.C(O)(C(F)(F)F)=O.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>>[CH3:31][C:30]1[N:20]2[C:15]3[CH:14]=[C:13]([C:10]4[CH:9]=[CH:8][C:7]([C:2](=[O:3])[CH3:1])=[CH:12][CH:11]=4)[NH:33][C:16]=3[N:17]=[CH:18][C:19]2=[N:21][CH:29]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 58382060HCID 58382060, compound

Product 1

HCID 58382287HCID 58382287, compoundYield 57.2%

Procedure

tert-Butyl 6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl(2-oxopropyl)carbamate (0.425 g, 0.729 mmol) was stirred in TFA (4.0 mL, 52 mmol). To the mixture was added TFAA (4 mL, 28.3 mmol) and the reaction stirred for about 20 h at rt. The solvents were removed under vacuum and 1,4-dioxane (12 mL) was added along with concentrated NH4OH (8 mL). The mixture was stirred for about 3 h. The resulting solid was collected by vacuum filtration washed with water and dried under vacuum at about 50° C. in the presence of P2O5 to a constant weight give 1-(4-(8-methyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-2-yl)phenyl)ethanone (0.121 g, 57%): LC/MS (Table 2, Method h) Rt=1.06 min.; MS m/z: 291 (M+H)+.

Workup

  1. customThe solvents were removed under vacuum and 1,4-dioxane (12 mL)
  2. additionwas added along with concentrated NH4OH (8 mL)
  3. stirringThe mixture was stirred for about 3 h
  4. filtrationThe resulting solid was collected by vacuum filtration
  5. washwashed with water
  6. dry with materialdried under vacuum at about 50° C. in the presence of P2O5 to a constant weight

Sources & evidence

ORD record
ord-d10d9f6049304d00a244e37b717b8917
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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