Trifluoroacetic acid → (R)-(1-isopropyl-7-(methylsulfonyl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazin-8-yl)methyl acetate

HRID 1521516Notes

Reaction equation

HRID 1521516 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([O:11][CH2:12][C:13]1[C:14]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:15][C:16]2[N:20]3[CH2:21][CH2:22][N:23](C(OC(C)(C)C)=O)[C@H:24]([CH:25]([CH3:27])[CH3:26])[C:19]3=[N:18][C:17]=2[CH:35]=1)(=[O:10])[CH3:9]>C(Cl)Cl>[C:8]([O:11][CH2:12][C:13]1[C:14]([S:36]([CH3:39])(=[O:37])=[O:38])=[CH:15][C:16]2[N:20]3[CH2:21][CH2:22][NH:23][C@H:24]([CH:25]([CH3:26])[CH3:27])[C:19]3=[N:18][C:17]=2[CH:35]=1)(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89815908(R)-tert-butyl 8-(acetoxymethyl)-1-isopropyl-7-(methylsulfonyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrazine-2(1H)-carboxylate

Product 1

HCID 89816096(R)-(1-isopropyl-7-(methylsulfonyl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazin-8-yl)methyl acetateYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added dropwise to a solution containing (R)-tert-butyl 8-(acetoxymethyl)-1-isopropyl-7-(methylsulfonyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrazine-2(1H)-carboxylate (210 mg, 0.452 mmol) in DCM (5 mL) at rt. The mixture was stirred at rt for 2 h. TLC showed compound 3 was consumed completely. The solvents were removed under reduced pressure at 30° C. and then DCM (10 mL) was added. The mixture was neutralized by sat. NaHCO3 solution to pH=8. The mixture was extracted with DCM (3×20 mL) and the combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under vacuum to afford (R)-(1-isopropyl-7-(methylsulfonyl)-1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazin-8-yl)methyl acetate (160 mg, 97.1% yield) as a white solid, which was used directly for the next step without further purification.

Workup

  1. customwas consumed completely
  2. customThe solvents were removed under reduced pressure at 30° C.
  3. additionDCM (10 mL) was added
  4. extractionThe mixture was extracted with DCM (3×20 mL)
  5. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1b938f487915410384a847ba91792c13
Source dataset
uspto-grants-2015_07
Patent number
US09073931B2

Reaction notes

Loading…