Trifluoroacetic acid → 6-chloro-2-fluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(3-(4-methoxyphenoxy)propylsulfonamido)benzamide

HRID 1943952Notes

Reaction equation

HRID 1943952 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:12]=[C:13]3[C:19]([O:20][CH3:21])=[N:18][N:17](CC4C=CC(OC)=CC=4)[C:14]3=[N:15][CH:16]=2)=[O:9])=[C:6]([F:31])[C:5]([NH:32][S:33]([CH2:36][CH2:37][CH2:38][O:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=2)(=[O:35])=[O:34])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>>[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:12]=[C:13]3[C:19]([O:20][CH3:21])=[N:18][NH:17][C:14]3=[N:15][CH:16]=2)=[O:9])=[C:6]([F:31])[C:5]([NH:32][S:33]([CH2:36][CH2:37][CH2:38][O:39][C:40]2[CH:41]=[CH:42][C:43]([O:46][CH3:47])=[CH:44][CH:45]=2)(=[O:35])=[O:34])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 670888896-chloro-2-fluoro-N-(3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(3-(4-methoxyphenoxy)propylsulfonamido)benzamide

Product 1

HCID 670890366-chloro-2-fluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(3-(4-methoxyphenoxy)propylsulfonamido)benzamideYield 97.5%

Conditions

Temperature
80 °C

Procedure

A 100 mL, round-bottomed flask was charged with 6-chloro-2-fluoro-N-(3-methoxy-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(3-(4-methoxyphenoxy)propylsulfonamido)benzamide (228.3 mg, 0.33 mmol) and TFA (0.5 mL). The reaction mixture was stirred at 80° C. until LC-MS showed that the starting material had been consumed (overnight). Then the CF3COOH was removed under reduced pressure. The residue was purified by silica gel chromatography (EtOAc/hexane from 1/4 to 1/0, v/v) to afford 6-chloro-2-fluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(3-(4-methoxyphenoxy)propylsulfonamido)benzamide (181.4 mg, 96.38%). LRMS (APCI pos): >95% purity, 254 nm, m/e 564.1 and 566.1 (M+1).

Workup

  1. customhad been consumed (overnight)
  2. customThen the CF3COOH was removed under reduced pressure
  3. customThe residue was purified by silica gel chromatography (EtOAc/hexane from 1/4 to 1/0

Sources & evidence

ORD record
ord-db74f49a84b043ae98067397195aaaa5
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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