Trifluoroacetic acid → N-(3-fluoro-4-(3-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide

HRID 2241349Notes

Reaction equation

HRID 2241349 reaction equation
[CH3:1][O:2][C:3]1[CH:58]=[CH:57][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]5[C:32](=[O:33])[N:31]([C:34]6[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=6)[N:30]=[CH:29][CH:28]=5)=[O:26])=[CH:20][C:19]=4[F:41])=[C:11]3[C:10]([N:42]3[CH2:46][CH:45]4[CH2:47][N:48](C(OC(C)(C)C)=O)[CH2:49][CH:44]4[CH2:43]3)=[N:9]2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:41][C:19]1[CH:20]=[C:21]([NH:24][C:25]([C:27]2[C:32](=[O:33])[N:31]([C:34]3[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=3)[N:30]=[CH:29][CH:28]=2)=[O:26])[CH:22]=[CH:23][C:18]=1[O:17][C:16]1[CH:15]=[CH:14][N:13]=[C:12]2[N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:58][CH:57]=3)[N:9]=[C:10]([N:42]3[CH2:46][CH:45]4[CH:44]([CH2:49][NH:48][CH2:47]4)[CH2:43]3)[C:11]=12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68512270tert-butyl 5-(1-(4-methoxybenzyl)-4-(2-fluoro-4-(1-(4-fluorophenyl)-6-oxo-1,6-dihydropyridazine-5-carboxamido)phenoxy)-1H-pyrazolo[3,4-b]pyridin-3-yl)-hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

Product 1

HCID 68512954N-(3-fluoro-4-(3-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamideYield 37.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round-bottomed flask was charged with tert-butyl 5-(1-(4-methoxybenzyl)-4-(2-fluoro-4-(1-(4-fluorophenyl)-6-oxo-1,6-dihydropyridazine-5-carboxamido)phenoxy)-1H-pyrazolo[3,4-b]pyridin-3-yl)-hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (42.5 mg, 0.0537 mmol), 2,2,2-trifluoroacetic acid (123 mg, 1.07 mmol) and CH2Cl2 (10 mL). The reaction mixture was stirred at ambient temperature for 4 hours. The solvent was removed and the residue was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 50/1 to 10/1, v/v) to give product (13.8 mg, 37.2%). LRMS (APCI neg): m/e 690 (M).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 50/1 to 10/1

Sources & evidence

ORD record
ord-5de18bd28c7f4febbe02e837f9c334da
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

Loading…