Trifluoroacetic acid → HCID 86645580, compound

HRID 2383438Notes

Reaction equation

HRID 2383438 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].COC1C=CC(C[N:15]2[C:19]3[N:20]=[CH:21][C:22]4[CH2:23][N:24]([C:28](=[O:37])[C@H:29]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[NH3+:30])[CH2:25][CH2:26][C:27]=4[C:18]=3[CH:17]=[N:16]2)=CC=1.[CH3:40][O:41][C:42]1[CH:78]=[CH:77][C:45]([CH2:46][N:47]2[C:51]3[N:52]=[CH:53][C:54]4[CH2:55][N:56]([C:60](=[O:76])[C@@H:61]([NH:68]C(=O)OC(C)(C)C)[C:62]5[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=5)[CH2:57][CH2:58][C:59]=4[C:50]=3[CH:49]=[N:48]2)=[CH:44][CH:43]=1.[F:79][C:80]([F:85])([F:84])[C:81]([OH:83])=[O:82]>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[CH:17]1[C:18]2[C:27]3[CH2:26][CH2:25][N:24]([C:28](=[O:37])[C@H:29]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[NH3+:30])[CH2:23][C:22]=3[CH:21]=[N:20][C:19]=2[NH:15][N:16]=1.[F:79][C:80]([F:85])([F:84])[C:81]([O-:83])=[O:82].[CH3:40][O:41][C:42]1[CH:43]=[CH:44][C:45]([CH2:46][N:47]2[C:51]3[N:52]=[CH:53][C:54]4[CH2:55][N:56]([C:60](=[O:76])[C@H:61]([C:62]5[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=5)[NH3+:68])[CH2:57][CH2:58][C:59]=4[C:50]=3[CH:49]=[N:48]2)=[CH:77][CH:78]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 59490352HCID 59490352, compoundHCID 86645580HCID 86645580, compound

Product 2

HCID 86645579HCID 86645579, compoundHCID 86645580HCID 86645580, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Synthesis of (S)-2-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-oxo-1-phenylethanaminium 2,2,2-trifluoroacetate. To a solution of (S)-tert-butyl 2-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-oxo-1-phenylethylcarbamate (0.23 g, 0.43 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (3 mL). The reaction was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and the crude product was purified using reverse phase HPLC to give the pure desired product (S)-2-(3-(4-methoxybenzyl)-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7(6H)-yl)-2-oxo-1-phenylethanaminium 2,2,2-trifluoroacetate as a pale yellow solid (0.131 g, 50%). M.p.>115° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.60 (brs, 2H), 8.45/8.15 (s, 1H, rotamers), 8.12/8.08 (s, 1H, rotamers), 7.55-7.33 (m, 5H), 7.17 (m, 2H), 6.82 (m, 2H), 5.75 (m, 1H), 5.55 (s, 2H), 4.97-4.35 (m, 2H), 4.02/3.74 (m, 2H, rotamers), 3.01/2.30 (m, 2H, rotamers); LC-Mass: m/e 428.57 (M+H). LCMS [M+H]: 428.

Workup

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

Sources & evidence

ORD record
ord-9f188f07237e4424b9ec29daedb9fd23
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

Loading…