Trifluoroacetic acid → HCID 178521319, compound

HRID 870598Notes

Reaction equation

HRID 870598 reaction equation
FC(F)(F)C(O)=O.[CH2:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH:9]1[NH:17][C:18]1[N:19]=[CH:20][C:21]2[CH2:26][N:25]([C:27](=[O:44])[CH2:28][N:29]([CH2:37][CH2:38][C:39]3[NH:43][N:42]=[N:41][CH:40]=3)C(=O)OC(C)(C)C)[CH2:24][C:22]=2[N:23]=1>ClCCl>[CH2:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH:9]1[NH:17][C:18]1[N:19]=[CH:20][C:21]2[CH2:26][N:25]([C:27](=[O:44])[CH2:28][NH:29][CH2:37][CH2:38][C:39]3[NH:43][N:42]=[N:41][CH:40]=3)[CH2:24][C:22]=2[N:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178453340HCID 178453340, compound

Product 1

HCID 178521319HCID 178521319, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (3 mL) slowly to a 0° C. solution containing tert-butyl {2-[2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidin-6-yl]-2-oxoethyl}[2-(1H-1,2,3-triazol-5-yl)ethyl]carbamate (0.15 g; 1.0 equiv; 0.297 mmoles) in dichloromethane (1 mL). Stir for 2 hours, then warm to ambient temperature and stir for 30 minutes. Concentrate the mixture and dissolve the residue in dichloromethane (20 mL). Add saturated sodium bicarbonate (20 mL), brine (20 mL), and water (50 mL), and extract with dichloromethane (6×20 mL). Dry the combined organic extracts over magnesium sulfate, filter, and concentrate to afford 1-[2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidin-6-yl]-2-{[2-(1H-1,2,3-triazol-5-yl)-ethyl]amino}ethanone (0.093 g; 77%) as a yellowish foam: MS (m/z): 405(M+1).

Workup

  1. stirringstir for 30 minutes
  2. concentrationConcentrate the mixture
  3. dissolutiondissolve the residue in dichloromethane (20 mL)
  4. extractionAdd saturated sodium bicarbonate (20 mL), brine (20 mL), and water (50 mL), and extract with dichloromethane (6×20 mL)
  5. dry with materialDry the combined organic extracts over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-72d735bbee644682a5cd516c3e495384
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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