Trifluoroacetic acid → (S)-2-(4-chlorophenyl)-3-(isopropylamino)-1-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-1-one

HRID 79547Notes

Reaction equation

HRID 79547 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:21](=[O:43])[N:22]2[CH2:27][CH2:26][N:25]([C:28]3[C:33]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:32][N:31]=[C:30]4[NH:40][CH:41]=[CH:42][C:29]=34)[CH2:24][CH2:23]2)[CH2:9][N:10]([CH:18]([CH3:20])[CH3:19])C(=O)OC(C)(C)C)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH2:9][NH:10][CH:18]([CH3:20])[CH3:19])[C:21]([N:22]2[CH2:23][CH2:24][N:25]([C:28]3[C:33]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:32][N:31]=[C:30]4[NH:40][CH:41]=[CH:42][C:29]=34)[CH2:26][CH2:27]2)=[O:43])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 68764607(S)-tert-Butyl 2-(4-chlorophenyl)-3-oxo-3-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)propyl(isopropyl)carbamate

Product 1

HCID 44198998(S)-2-(4-chlorophenyl)-3-(isopropylamino)-1-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-1-oneYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 2-(4-chlorophenyl)-3-oxo-3-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)propyl(isopropyl)carbamate (0.003 g, 0.0050 mmol) was placed in DCM (2 mL) at room temperature. TFA (0.4 mL) was then added, and the reaction was stirred for 1 hour. The reaction was concentrated to dryness. The crude residue was dissolved in minimal DCM and added dropwise to a stirring solution of 1M HCl in ether (10 mL). The solid product was then filtered, washed with ether, and dried to give (S)-2-(4-chlorophenyl)-3-(isopropylamino)-1-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)propan-1-one (0.001 g, 40% yield) as the dihydrochloride salt. MS ESI (+) m/z 503 detected.

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. dissolutionThe crude residue was dissolved in minimal DCM
  3. additionadded dropwise to a stirring solution of 1M HCl in ether (10 mL)
  4. filtrationThe solid product was then filtered
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-25a472a48c9c4af385f07dfa12b6d664
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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