Trifluoroacetic acid → (s)-2-(4-Chlorophenyl)-1-(4-(5-(3,4-dimethoxyphenyl)-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(isopropylamino)propan-1-one

HRID 79541Notes

Reaction equation

HRID 79541 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:21]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[C:34]([C:35]4[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([O:43][CH3:44])[CH:36]=4)=[CH:33][N:32]=[C:31]4[NH:45][CH:46]=[CH:47][C:30]=34)[CH2:25][CH2:24]2)=[O:22])[CH2:9][N:10]([CH:18]([CH3:20])[CH3:19])C(=O)OC(C)(C)C)=[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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([CH2:9][NH:10][CH:18]([CH3:20])[CH3:19])[C:21]([N:23]2[CH2:24][CH2:25][N:26]([C:29]3[C:34]([C:35]4[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([O:43][CH3:44])[CH:36]=4)=[CH:33][N:32]=[C:31]4[NH:45][CH:46]=[CH:47][C:30]=34)[CH2:27][CH2:28]2)=[O:22])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 68761848(S)-tert-butyl 2-(4-chlorophenyl)-3-(4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate

Product 1

HCID 59627016(s)-2-(4-Chlorophenyl)-1-(4-(5-(3,4-dimethoxyphenyl)-1h-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-(isopropylamino)propan-1-oneYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-tert-Butyl 2-(4-chlorophenyl)-3-(4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-3-oxopropyl(isopropyl)carbamate (0.013 g, 0.020 mmol) was placed in DCM (3 mL). TFA (0.3 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 dropwise to a stirring solution of 1M HCl in ether. The solid product was filtered, washed with ether, and dried to give (S)-2-(4-chlorophenyl)-1-(4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)-3-(isopropylamino)propan-1-one (0.009 g, 72% yield) as the dihydrochloride salt. MS ESI (+) m/z 563 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-a60d0351fe2d4eff84ae337cf236a9da
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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