Trifluoroacetic acid → [5-(1-Cyclopropyl-piperidin-4-yloxy)-1H-pyrrolo[2,3-b]pyridin-2-yl]-morpholin-4-yl-methanone

HRID 1437704Notes

Reaction equation

HRID 1437704 reaction equation
C(OC([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([O:17][CH:18]3[CH2:23][CH2:22][N:21]([CH:24]4[CH2:26][CH2:25]4)[CH2:20][CH2:19]3)[CH:16]=[C:11]2[CH:10]=[C:9]1[C:27]([N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)=[O:28])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH:24]1([N:21]2[CH2:22][CH2:23][CH:18]([O:17][C:15]3[CH:16]=[C:11]4[CH:10]=[C:9]([C:27]([N:29]5[CH2:34][CH2:33][O:32][CH2:31][CH2:30]5)=[O:28])[NH:8][C:12]4=[N:13][CH:14]=3)[CH2:19][CH2:20]2)[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68423474HCID 68423474, compound

Product 1

HCID 16727355[5-(1-Cyclopropyl-piperidin-4-yloxy)-1H-pyrrolo[2,3-b]pyridin-2-yl]-morpholin-4-yl-methanoneYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of 0.16 g (0.34 mmol) 5-(1-cyclopropyl-piperidin-4-yloxy)-2-(morpholine-4-carbonyl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester in 2 ml dichloromethane was cooled down to 0° C. and treated with 0.52 ml (0.8 g, 6.8 mmol) trifluoroacetic acid. The cooling bath was removed and after 1 hour at room temperature the solution was evaporated and the residue was flash-chromatographed on silica gel with dichloromethane:methanol:ammonia (9:1:0.1 v/v) as eluant to give 0.1 g (83%) of the desired compound as a colorless solid.

Workup

  1. customThe cooling bath was removed and after 1 hour at room temperature the solution
  2. customwas evaporated
  3. customthe residue was flash-chromatographed on silica gel with dichloromethane:methanol:ammonia (9:1:0.1 v/v) as eluant

Sources & evidence

ORD record
ord-2857442c2b9d40038ba05edc9b4d1277
Source dataset
uspto-grants-2009_11
Patent number
US07622466B2

Reaction notes

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