Trifluoroacetic acid → HCID 118272498, compound

HRID 588208Notes

Reaction equation

HRID 588208 reaction equation
[C:1]([O:4][CH2:5][C:6]1[C:11]2[C:12]([O:15][CH3:16])=[N:13][NH:14][C:10]=2[CH:9]=[C:8]([NH:17][C:18]([NH:20][C@@H:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:22])=[O:19])[N:7]=1)(=[O:3])[CH3:2].[B-](F)(F)(F)[F:30].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.C(O)(C(F)(F)F)=O>CO>[C:1]([O:4][CH2:5][C:6]1[C:11]2[C:12]([O:15][CH3:16])=[N:13][NH:14][C:10]=2[C:9]([F:30])=[C:8]([NH:17][C:18]([NH:20][C@@H:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH3:22])=[O:19])[N:7]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 2724933SelectfluorHCID 76071450HCID 76071450, compound2×

Product 1

HCID 118272498HCID 118272498, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-(3-methoxy-6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl acetate (108 mg, 0.282 mmol, Example 257, derived from Intermediate 41B according to Scheme 3/Method A) was dissolved in MeOH (1 mL) and charged with selectfluor (150 mg, 0.423 mmol). The reaction was allowed to stir overnight at rt. The solvents were removed in vacuo and the residue was purified on RP-HPLC 30×150 mm column (25-60% CH3CN/H2O w/0.1% TFA) to provide (R)-(7-fluoro-3-methoxy-6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-4-yl)methyl acetate (60 mg, 0.149 mmol, 53.1% yield) as TFA salt.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was purified on RP-HPLC 30×150 mm column (25-60% CH3CN/H2O w/0.1% TFA)

Sources & evidence

ORD record
ord-8384bcb444c245618a9d8f563f54bdb5
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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