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

HRID 79610Notes

Reaction equation

HRID 79610 reaction equation
[CH3:1][CH:2]([CH3:38])[C@@H:3]([NH:30]C(=O)OC(C)(C)C)[C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]3[NH:18][CH:19]=[C:20]([NH:21][C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=4)[C:13]=23)[CH2:8][CH2:7]1)=[O:5].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:30][C@H:3]([CH:2]([CH3:38])[CH3:1])[C:4]([N:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]3[NH:18][CH:19]=[C:20]([NH:21][C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=4)[C:13]=23)[CH2:10][CH2:11]1)=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68784483(R)-tert-Butyl 3-methyl-1-(4-(3-(nicotinamido)-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)-1-oxobutan-2-ylcarbamate

Product 1

HCID 44198121(R)-N-(4-(4-(2-amino-3-methylbutanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamideYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-tert-Butyl 3-methyl-1-(4-(3-(nicotinamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-1-oxobutan-2-ylcarbamate (0.014 g, 0.027 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 then added dropwise to a stirring solution of 1M HCl in ether. The resulting solid was filtered, washed with ether, and dried to give (R)—N-(4-(4-(2-amino-3-methylbutanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (0.009 g, 63% yield) as the trihydrochloride salt. MS APCI (+) m/z 422 detected.

Workup

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

Sources & evidence

ORD record
ord-c423d338a0b84655bea6f853d9a329b1
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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