Trifluoroacetic acid → HCID 178520575, compound

HRID 870585Notes

Reaction equation

HRID 870585 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[CH2:27][N:26]([C:28](=[O:45])[CH2:29][CH2:30][CH2:31][CH2:32][C:33]3[N:37](C(OC(C)(C)C)=O)[CH:36]=[N:35][CH:34]=3)[CH2:25][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[CH2:27][N:26]([C:28](=[O:45])[CH2:29][CH2:30][CH2:31][CH2:32][C:33]3[N:37]=[CH:36][NH:35][CH:34]=3)[CH2:25][CH2:24][C:22]=2[N:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86726546tert-butyl 5-[5-[2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]-5-oxo-pentyl]imidazole-1-carboxylate

Product 1

HCID 178520575HCID 178520575, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic acid (1.5 mL) to a solution of tert-butyl 5-[5-[2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]-5-oxo-pentyl]imidazole-1-carboxylate (0.030 g; 0.058 mmoles) in dichloromethane (8 mL). Stir the reaction at room temperature for 2 hr. Concentrate the mixture and add saturated sodium bicarbonate (10 mL) and water (20 mL), then extract with dichloromethane (3×20 mL). Wash the combined organic extracts with brine, dry over sodium sulfate, filter, and concentrate. Purify the crude product by column chromatography (0 to 10% methanol in dichloromethane) to afford 1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-5-(1H-imidazol-4-yl)pentan-1-one (0.020 g; 83%) as a white solid: MS (m/z): 417 (M+1).

Workup

  1. customthe reaction at room temperature for 2 hr
  2. concentrationConcentrate the mixture
  3. additionadd saturated sodium bicarbonate (10 mL) and water (20 mL)
  4. extractionextract with dichloromethane (3×20 mL)
  5. washWash the combined organic extracts with brine
  6. dry with materialdry over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify the crude product by column chromatography (0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-2cc3819e56584561956fabaa1ceac193
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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