Trifluoroacetic acid → HCID 67125813, compound

HRID 2042409Notes

Reaction equation

HRID 2042409 reaction equation
[CH3:1][C:2]1[C:3]2[O:23][CH:22]=[CH:21][C:4]=2[C:5]([N:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:1][C:2]1[C:3]2[O:23][CH:22]=[CH:21][C:4]=2[C:5]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 67125779HCID 67125779, compound

Product 1

HCID 67125813HCID 67125813, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A stirred solution of tert-butyl 4-(7-methyl-furo[3,2-c]pyridin-4-yl)-piperazine-1-carboxylate (step A) (2.34 g, 7.37 mmol) in dichloromethane (4.1 ml) was cooled to 0° C., trifluoroacetic acid (8.41 g, 5.68 ml, 73.7 mmol) was added drop wise and the reaction mixture was allowed to stir for 10 min at 0° C. and for 30 min at room temperature. The solution was poured onto ice and 2N sodium carbonate solution (50 ml) and extracted with dichloromethane (2×25 ml). The combined organic layers were washed with brine (30 mL), dried (MgSO4) and evaporated. The crude product (1.59 g) was further purified by flash chromatography on silica gel (100% dichloromethane/MeOH/NH4OH 80:10:1) to yield 7-methyl-4-(piperazin-1-yl)-furo[3,2-c]pyridine as a yellow solid (1.27 g, 79%), MS (ISP) m/z=218.4 [(M+H)+], mp 111.5° C.

Workup

  1. extractionextracted with dichloromethane (2×25 ml)
  2. washThe combined organic layers were washed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude product (1.59 g) was further purified by flash chromatography on silica gel (100% dichloromethane/MeOH/NH4OH 80:10:1)

Sources & evidence

ORD record
ord-05393eb23f4a4c91a84196bcd4a80fc5
Source dataset
uspto-grants-2013_11
Patent number
US08586579B2

Reaction notes

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