Trifluoroacetic acid → (R)-4-amino-2-(4-chlorophenyl)-4-methyl-1-(4-(3-methyl-5-phenyl-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)pentan-1-one

HRID 79558Notes

Reaction equation

HRID 79558 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][CH:38]=[CH:37][CH:36]=4)=[CH:33][N:32]=[C:31]4[NH:41][CH:42]=[C:43]([CH3:44])[C:30]=34)[CH2:25][CH2:24]2)=[O:22])[CH2:9][C:10]([NH:13]C(=O)OC(C)(C)C)([CH3:12])[CH3:11])=[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>[NH2:13][C:10]([CH3:12])([CH3:11])[CH2:9][C@H:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:21]([N:23]1[CH2:24][CH2:25][N:26]([C:29]2[C:34]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[CH:33][N:32]=[C:31]3[NH:41][CH:42]=[C:43]([CH3:44])[C:30]=23)[CH2:27][CH2:28]1)=[O:22]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 68763597HCID 68763597, compound

Product 1

HCID 44199001(R)-4-amino-2-(4-chlorophenyl)-4-methyl-1-(4-(3-methyl-5-phenyl-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)pentan-1-oneYield 101.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-tert-Butyl 4-(4-chlorophenyl)-2-methyl-5-(4-(3-methyl-5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-5-oxopentan-2-ylcarbamate (0.040 g, 0.065 mmol) was placed in DCM (3 mL). TFA (0.3 mL) was then added. The reaction was stirred for 1 hour and then concentrated to dryness. The resulting oil was dissolved in minimal DCM, and added to a stirring solution of 1M HCl in ether. The resulting solid was collected by filtration, washed with ether, and dried to give (R)-4-amino-2-(4-chlorophenyl)-4-methyl-1-(4-(3-methyl-5-phenyl-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)pentan-1-one (0.034 g, 89% yield) as the dihydrochloride salt. MS ESI (+) m/z 517 detected.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe resulting oil was dissolved in minimal DCM
  3. additionadded to a stirring solution of 1M HCl in ether
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-12bbb8f62eb54e80ad993a1ff8eecd2a
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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