Trifluoroacetic acid → HCID 44198876, compound

HRID 79521Notes

Reaction equation

HRID 79521 reaction equation
[Br:1][C:2]1[C:3]([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:38])[C@@H:18]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)[CH2:19][N:20]([CH:28]([CH3:30])[CH3:29])C(=O)OC(C)(C)C)[CH2:13][CH2:12]2)=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=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>[Br:1][C:2]1[C:3]([N:11]2[CH2:12][CH2:13][N:14]([C:17](=[O:38])[C@@H:18]([C:31]3[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=3)[CH2:19][NH:20][CH:28]([CH3:30])[CH3:29])[CH2:15][CH2:16]2)=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 68764847(5)-Tert-butyl 3-(4-(5-bromo-1h-pyrrolo [2,3-b]pyridin-4-yl)piperazin-1-yl)-2-(4-chlorophenyl)-3-oxopropyl(isopropyl)carbamate

Product 1

HCID 44198876HCID 44198876, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 3-(4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-2-(4-chlorophenyl)-3-oxopropyl(isopropyl)carbamate (0.040 g, 0.066 mmol) was placed in DCM (3 mL). TFA (0.3 mL) was then added. The reaction was stirred at room temperature for 1 hour. The reaction was then concentrated to dryness, dissolved in minimal DCM, and added dropwise to a stirring solution of 1M HCl in ether. The solid product was filtered, washed with ether, and dried to give (S)-1-(4-(5-bromo-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)-2-(4-chlorophenyl)-3-(isopropylamino)propan-1-one (0.03 g, 90% yield) as the dihydrochloride salt. MS ESI (+) m/z 505 detected.

Workup

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

Sources & evidence

ORD record
ord-776922a3a00e48eb9cbeb627f6da39bf
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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