Trifluoroacetic acid → (R)-3-Amino-N-methyl-N-(1-(pyridin-4-yl)piperidin-4-yl)-2,3-dihydro-1H-indene-5-carboxamide

HRID 1193419Notes

Reaction equation

HRID 1193419 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][N:9]([CH:29]1[CH2:34][CH2:33][N:32]([C:35]2[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=2)[CH2:31][CH2:30]1)[C:10]([C:12]1[CH:20]=[C:19]2[C:15]([CH2:16][CH2:17][C@H:18]2[NH:21]C(=O)OC(C)(C)C)=[CH:14][CH:13]=1)=[O:11]>ClCCl>[NH2:21][C@H:18]1[C:19]2[C:15](=[CH:14][CH:13]=[C:12]([C:10]([N:9]([CH3:8])[CH:29]3[CH2:30][CH2:31][N:32]([C:35]4[CH:36]=[CH:37][N:38]=[CH:39][CH:40]=4)[CH2:33][CH2:34]3)=[O:11])[CH:20]=2)[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66798862(R)-tert-Butyl 6-(methyl(1-(pyridin-4-yl)piperidin-4-yl)carbamoyl)-2,3-dihydro-1H-inden-1-ylcarbamate

Product 1

HCID 66798813(R)-3-Amino-N-methyl-N-(1-(pyridin-4-yl)piperidin-4-yl)-2,3-dihydro-1H-indene-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 ml) was added dropwise at 0° C. to a solution of (R)-tert-butyl 6-(methyl(1-(pyridin-4-yl)piperidin-4-yl)carbamoyl)-2,3-dihydro-1H-inden-1-ylcarbamate (0.2 g, 0.44 mmol, 1 eq) in dichloromethane (5 ml), and stirring was carried out for 1 h at RT. Then the solvent was concentrated under reduced pressure. The residue was taken up in dichloromethane and concentrated again. Then the TFA salt was stirred for 1 h with Amberlyst-21 in MeOH (10 ml) and filtered. The filtrate was concentrated under reduced pressure and used in the next stage without being purified further.

Workup

  1. concentrationThen the solvent was concentrated under reduced pressure
  2. concentrationconcentrated again
  3. stirringThen the TFA salt was stirred for 1 h with Amberlyst-21 in MeOH (10 ml)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customwithout being purified further

Sources & evidence

ORD record
ord-9c6d1c705bfd4707affe6bb773a60fdc
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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