Trifluoroacetic acid → HCID 178462161, compound

HRID 571422Notes

Reaction equation

HRID 571422 reaction equation
[C:1]([CH2:3][C:4]1[C:8]2[CH:9]=[N:10][C:11]([NH:13][C:14]([NH:16][C@@H:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:18])=[O:15])=[CH:12][C:7]=2[N:6](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:5]=1)#[N:2].C(O)(C(F)(F)F)=O>>[C:1]([CH2:3][C:4]1[C:8]2[CH:9]=[N:10][C:11]([NH:13][C:14]([NH:16][C@@H:17]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH3:18])=[O:15])=[CH:12][C:7]=2[NH:6][N:5]=1)#[N:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117601641HCID 117601641, compound

Product 1

HCID 178462161HCID 178462161, compoundYield 58.3%

Procedure

(R)-1-(3-(cyanomethyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (20 mg, 0.036 mmol) was dissolved in TFA (0.274 ml, 3.55 mmol) and stirred for 30 m at rt. The solvents were removed in vacuo and the residue purified by reverse-phase HPLC to provide pure (R)-1-(3-(cyanomethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (9 mg, 0.021 mmol, 58.3% yield). MS ESI Calc'd for C17H16N6O [M+H]+ 321, found 321.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-0306f58cd1ee46dcafec7e2d386d2493
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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