Trifluoroacetic acid → HCID 44198750, compound

HRID 79517Notes

Reaction equation

HRID 79517 reaction equation
C(OC([NH:8][C@H:9]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18]2[C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][N:21]=[C:20]3[NH:28][CH:29]=[CH:30][C:19]=23)[CH2:14][CH2:13]1)=[O:11])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C@H:9]([CH2:31][C:32]1[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=1)[C:10]([N:12]1[CH2:13][CH2:14][N:15]([C:18]2[C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][N:21]=[C:20]3[NH:28][CH:29]=[CH:30][C:19]=23)[CH2:16][CH2:17]1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68765221(R)-Methyl 4-(4-(2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo [2,3-b]pyridine-5-carboxylate

Product 1

HCID 44198750HCID 44198750, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-Methyl 4-(4-(2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (0.025 g, 0.046 mmol) was placed in DCM (3 mL) at room temperature. TFA (0.3 mL) was then added. The reaction was stirred at room temperature for 1 hour and then concentrated. The resulting residue was dissolved in minimal DCM and added to a stirring solution of 1M HCl in ether. The resulting solid (R)-methyl 4-(4-(2-amino-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (0.015 g, 74% yield) was collected and dried as the dihydrochloride salt. MS ESI (+) m/z 442 detected.

Workup

  1. concentrationconcentrated
  2. dissolutionThe resulting residue was dissolved in minimal DCM
  3. additionadded to a stirring solution of 1M HCl in ether

Sources & evidence

ORD record
ord-833cc291fc974a7985c55c420f2d3778
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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