Trifluoroacetic acid → HCID 44198253, compound

HRID 79623Notes

Reaction equation

HRID 79623 reaction equation
[C:1]([NH:9][C:10]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:17]=2[N:19]2[CH2:24][CH2:23][N:22]([C:25](=[O:36])[CH2:26][CH2:27][NH:28]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>[NH2:28][CH2:27][CH2:26][C:25]([N:22]1[CH2:23][CH2:24][N:19]([C:17]2[C:16]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=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)[CH2:20][CH2:21]1)=[O:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68784056HCID 68784056, compound

Product 1

HCID 44198253HCID 44198253, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-(4-(3-(nicotinamido)-5-phenyl-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-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (0.008 g, 39% yield) as the trihydrochloride salt. MS APCI (+) m/z 470 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-b14eb1a43aff4c5489a534c42de61d93
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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