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

HRID 79605Notes

Reaction equation

HRID 79605 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:32]C(=O)OC(C)(C)C)[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]4[NH:24][CH:25]=[C:26]([NH:27][C:28](=[O:31])[CH2:29][OH:30])[C:19]=34)[CH2:14][CH2:13]2)=[O:11])=[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>[NH2:32][C@H:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C:10]([N:12]1[CH2:13][CH2:14][N:15]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]3[NH:24][CH:25]=[C:26]([NH:27][C:28](=[O:31])[CH2:29][OH:30])[C:19]=23)[CH2:16][CH2:17]1)=[O:11]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 68760357HCID 68760357, compound

Product 1

HCID 44197986(R)-N-(4-(4-(2-amino-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-hydroxyacetamideYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-tert-Butyl 3-(4-chlorophenyl)-1-(4-(3-(2-hydroxyacetamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-1-oxopropan-2-ylcarbamate (0.040 g, 0.072 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, and the resulting residue was dissolved in minimal DCM. The solution was 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-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-hydroxyacetamide (0.030 g, 79% yield) as the dihydrochloride salt. MS APCI (+) m/z 457 detected.

Workup

  1. concentrationThe reaction was then concentrated to dryness
  2. dissolutionthe resulting residue was dissolved in minimal DCM
  3. additionThe solution was added 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-f09fc74d886b4ac294038238fda77de6
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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