Toluene → HCID 178474140, compound

HRID 2383481Notes

Reaction equation

HRID 2383481 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[C:23]3[C:22]4[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][C:17]=4[CH:16]=[N:15][C:14]=3[NH:13][N:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].C1(C)C=CC=CC=1>ClCCl>[F:31][C:32]([F:37])([F:36])[C:33]([O-:35])=[O:34].[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[C:23]3[C:22]4[CH2:21][CH2:20][NH2+:19][CH2:18][C:17]=4[CH:16]=[N:15][C:14]=3[NH:13][N:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 178474139HCID 178474139, compound

Product 1

HCID 178474140HCID 178474140, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 1-(3-acetamidophenyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate (0.108 g, 0.26 mmol) in dichloromethane (5 mL) was added trifluoroacetic acid (0.5 mL). The reaction was shaken overnight at room temperature. On completion, toluene (1 mL) was added and the solvent removed under reduced pressure. The crude product was purified using reverse phase HPLC (C-18 using TFA as a modifier) to give the desired product, 1-(3-acetamidophenyl)-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium 2,2,2-trifluoroacetate (0.042 g, 37%) as an off-white solid; M.p.=245° C. decomposition; 400 MHz 1H NMR (DMSO-d6) δ: 13.89 (br s, 1H), 10.13 (s, 1H), 9.16 (s, 1H), 8.43 (s, 1H), 8.01 (s, 1H), 7.56-7.5 (m, 1H), 7.48-7.4 (m, 1H), 7.28-7.22 (m, 1H), 4.43 (s, 2H), 3.4-3.3 (m, 2H), 3.1-3.0 (m, 2H), 2.08 (s, 3H); LCMS [M+H]: 308.

Workup

  1. customthe solvent removed under reduced pressure
  2. customThe crude product was purified

Sources & evidence

ORD record
ord-8e4ebf9c469a4ab1bb90069cd58767d4
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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