Trifluoroacetic acid → N-(4-(4-(2-amino acetyl)piperazin-1-yl)-5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide

HRID 79621Notes

Reaction equation

HRID 79621 reaction equation
[C:1]([NH:9][C:10]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:17]=2[N:19]2[CH2:24][CH2:23][N:22]([C:25](=[O:35])[CH2:26][NH:27]C(=O)OC(C)(C)C)[CH2:21][CH2:20]2)[NH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:27][CH2:26][C:25]([N:22]1[CH2:21][CH2:20][N:19]([C:17]2[C:16]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[CH:15][N:14]=[C:13]3[NH:12][CH:11]=[C:10]([NH:9][C:1](=[O:8])[C:2]4[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=4)[C:18]=23)[CH2:24][CH2:23]1)=[O:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68781181HCID 68781181, compound

Product 1

HCID 44198126N-(4-(4-(2-amino acetyl)piperazin-1-yl)-5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamideYield 38.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 2-(4-(3-(nicotinamido)-5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-2-oxoethylcarbamate (0.013 g, 0.023 mmol) was placed in DCM (3 mL) at room temperature. TFA (0.5 mL) was then added, and the reaction was stirred at room temperature for 1 hour. The reaction was then concentrated to dryness. The resulting residue was dissolved in minimal DCM and added to a stirring solution of 1M HCl in ether. The resulting solid product was filtered, washed with ether and dried to give N-(4-(4-(2-amino acetyl)piperazin-1-yl)-5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (0.004 g, 38% yield) as the trihydrochloride salt. MS APCI (+) m/z 456 detected.

Workup

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

Sources & evidence

ORD record
ord-7ebfff587b9b45fdb90f711154fe6407
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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