Trifluoroacetic acid → HCID 90027034, compound

HRID 2275041Notes

Reaction equation

HRID 2275041 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([C:16]2[CH:38]=[CH:37][C:19]3[N:20]([CH3:36])[C:21]([C:23]4[N:33]([CH2:34][CH3:35])[C:26]5=[N:27][CH:28]=[C:29]([O:31][CH3:32])[CH:30]=[C:25]5[CH:24]=4)=[N:22][C:18]=3[CH:17]=2)=[O:15])[CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([C:16]2[CH:38]=[CH:37][C:19]3[N:20]([CH3:36])[C:21]([C:23]4[N:33]([CH2:34][CH3:35])[C:26]5=[N:27][CH:28]=[C:29]([O:31][CH3:32])[CH:30]=[C:25]5[CH:24]=4)=[N:22][C:18]=3[CH:17]=2)=[O:15])[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118178618HCID 118178618, compound

Product 1

HCID 90027034HCID 90027034, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (R)-tert-butyl(1-(2-(1-ethyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-1-methyl-1H-benzo[d]imidazole-5-carbonyl)piperidin-3-yl)carbamate (24 mg, 0.045 mmol) in DCM (2 mL) was added TFA (2 mL, 26.0 mmol) dropwise with continuous stirring. The reaction was stirred at room temperature under nitrogen for 1 h. The reaction mixture was concentrated in vacuo before being dissolved in MeOH and purified by SPE on sulfonic acid (SCX) 1 g, first washing with MeOH and then eluting using a 10% NH3/MeOH solution to give the free base of the product. The appropriate fractions were combined and evaporated in vacuo before being azeotroped with cyclohexane to give the title compound as a pale yellow solid (13 mg).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionbefore being dissolved in MeOH
  3. custompurified by SPE on sulfonic acid (SCX) 1 g
  4. washfirst washing with MeOH
  5. washeluting
  6. customto give the free base of the product
  7. customevaporated in vacuo
  8. custombefore being azeotroped with cyclohexane

Sources & evidence

ORD record
ord-a3575abc3c624c8dac83e2378a4915fa
Source dataset
uspto-grants-2015_09
Patent number
US09127003B2

Reaction notes

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