Trifluoroacetic acid → N-(4-(4-(3-aminopropanoyl)piperazin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyri din-3-yl)nicotinamide

HRID 79618Notes

Reaction equation

HRID 79618 reaction equation
[Br:1][C:2]1[C:3]([N:20]2[CH2:25][CH2:24][N:23]([C:26](=[O:37])[CH2:27][CH2:28][NH:29]C(=O)OC(C)(C)C)[CH2:22][CH2:21]2)=[C:4]2[C:10]([NH:11][C:12](=[O:19])[C:13]3[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=3)=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:29][CH2:28][CH2:27][C:26]([N:23]1[CH2:22][CH2:21][N:20]([C:3]2[C:2]([Br:1])=[CH:7][N:6]=[C:5]3[NH:8][CH:9]=[C:10]([NH:11][C:12](=[O:19])[C:13]4[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=4)[C:4]=23)[CH2:25][CH2:24]1)=[O:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68764850HCID 68764850, compound

Product 1

HCID 44198124N-(4-(4-(3-aminopropanoyl)piperazin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyri din-3-yl)nicotinamideYield 90.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-(4-(5-bromo-3-(nicotinamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-oxopropylcarbamate (0.020 g, 0.035 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, 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 the product N-(4-(4-(3-aminopropanoyl)piperazin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyri din-3-yl)nicotinamide (0.015 g, 74% yield) as the trihydrochloride salt. MS APCI (+) m/z 473 detected.

Workup

  1. concentrationThe reaction was then concentrated to dryness
  2. dissolutiondissolved 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-285cda617afe4c3ba1f303080fe12a43
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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