Trifluoroacetic acid → HCID 66712194, compound

HRID 1262264Notes

Reaction equation

HRID 1262264 reaction equation
C(OC(N1CCCCC1[C:14]1[N:22]2[C:17]([CH:18]=[N:19][C:20]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[CH:26][CH:25]=3)=[N:21]2)=[CH:16][CH:15]=1)=O)(C)(C)C.F[C:37](F)(F)[C:38](O)=O>C(Cl)Cl>[N:30]1([C:27]2[CH:26]=[CH:25][C:24]([NH:23][C:20]3[N:19]=[CH:18][C:17]4=[CH:16][CH:15]=[C:14]([C:16]5[CH2:17][CH2:18][NH:19][CH2:37][CH:38]=5)[N:22]4[N:21]=3)=[CH:29][CH:28]=2)[CH2:31][CH2:32][O:33][CH2:34][CH2:35]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66712575HCID 66712575, compound

Product 1

HCID 66712194HCID 66712194, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 8 dram vial, [2-(4-Morpholin-4-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-piperidine-1-carboxylic acid tert-butyl ester (0.150 g, 0.315 mmol), Methylene chloride (5 mL) and Trifluoroacetic Acid (1 g, 9 mmol) were added and stirred at room temperature over night. The reaction was partitioned with Sat. NaHCO3 and DCM. The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum. The desired product was purified via ISCO column chromatography with DCM and methanol as eluant (0 to 10% methanol). The collected fractions afforded (4-Morpholin-4-yl-phenyl)-[7-(1,2,3,6-tetrahydro-pyridin-4-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine as a yellow solid.

Workup

  1. customThe reaction was partitioned with Sat. NaHCO3 and DCM
  2. customThe organic was separated
  3. washwashed with Brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe solid was filtered
  6. washwashed with DCM
  7. customThe solvent was removed under vacuum
  8. customThe desired product was purified via ISCO column chromatography with DCM and methanol as eluant (0 to 10% methanol)

Sources & evidence

ORD record
ord-55a653db47f54515b4a9d40d376f818e
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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