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

HRID 79602Notes

Reaction equation

HRID 79602 reaction equation
[C:1]([NH:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][C:12]=2[N:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:38])[C@H:21]([NH:30]C(=O)OC(C)(C)C)[CH2:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[CH2:16][CH2:15]2)[NH:7][CH:6]=1)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>C(Cl)Cl>[NH2:30][C@H:21]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=1)[C:20]([N:17]1[CH2:16][CH2:15][N:14]([C:12]2[CH:11]=[CH:10][N:9]=[C:8]3[NH:7][CH:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[C:13]=23)[CH2:19][CH2:18]1)=[O:38]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 68760828(R)-tert-butyl 1-(4-(3-acetamido-1H-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate

Product 1

HCID 44197985(R)-N-(4-(4-(2-amino-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)acetamideYield 104.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-tert-Butyl 1-(4-(3-acetamido-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(4-chlorophenyl)-1-oxopropan-2-ylcarbamate (0.047 g, 0.087 mmol) was placed in DCM (5 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 crude residue was then dissolved in minimal DCM and 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)acetamide (0.04 g, 90% yield) as the dihydrochloride salt. MS APCI (+) m/z 441 detected.

Workup

  1. concentrationThe reaction was then concentrated to dryness
  2. dissolutionThe crude residue was then 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-a6f29acef04b41cab785d953f97e1a22
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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