Trifluoroacetic acid → HCID 66711490, compound

HRID 1262124Notes

Reaction equation

HRID 1262124 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[N:26]=[CH:25][C:24]4=[CH:27][CH:28]=[C:29]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=5[O:36][CH3:37])[N:23]4[N:22]=3)=[C:16]([O:38][CH3:39])[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:37][O:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[C:29]1[N:23]2[C:24]([CH:25]=[N:26][C:21]([NH:20][C:17]3[CH:18]=[CH:19][C:14]([CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)=[CH:15][C:16]=3[O:38][CH3:39])=[N:22]2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66711689HCID 66711689, compound

Product 1

HCID 66711490HCID 66711490, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-{3-Methoxy-4-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperidine-1-carboxylic acid tert-butyl ester (650.00 mg, 1.227 mmol) was treated with trifluoroacetic acid (0.473 mL, 6.136 mmol) in methylene chloride (3 mL) at room temperature until complete reaction of starting material was observed by hplc analysis of reaction mixture. The reaction was quenched with minimum amount of saturated aqueous sodium carbonate, and was extracted extensively in dichloromethane. The combined organic extracts were dried over MgSO4 and then filtered. Evaporation of solvent under reduced pressure afforded [7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(2-methoxy-4-piperidin-4-yl-phenyl)-amine as a yellow foam (504 mg, 96%) which was used without further purification in the next step.

Workup

  1. customwas observed by hplc analysis of reaction mixture
  2. customThe reaction was quenched with minimum amount of saturated aqueous sodium carbonate
  3. extractionwas extracted extensively in dichloromethane
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. customEvaporation of solvent under reduced pressure

Sources & evidence

ORD record
ord-559ac83657a44784afcb8301aea163b3
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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