HCID 118271824, compound → HCID 118272007, compound

HRID 588181Notes

Reaction equation

HRID 588181 reaction equation
[F:1][CH:2]([F:44])[O: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>C(O)(C(F)(F)F)=O.CS(C)=O>[F:44][CH:2]([F:1])[O: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[NH:6][N:5]=1

Participants

4

Reactant 1

HCID 118271824HCID 118271824, compound

Product 1

HCID 118272007HCID 118272007, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (R)-1-(3-(difluoromethoxy)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (58.5 mg, 0.099 mmol) in TFA (2 mL) was stirred at room temperature for 2.5 h. The reaction mixture was diluted with DMSO (2 mL) and purified by mass-triggered reverse-phase HPLC. The fractions containing pure product were freebased with a PL-HCO3 cartridge and concentrated in vacuo to give (R)-1-(3-(difluoromethoxy)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. For C16H15F2N5O2 [M+1]+ 348. found 348. 1H NMR (500 MHz, DMSO-d6) δ 9.03 (s, 1H), 8.66 (s, 1H), 7.64 (m, 2H), 7.52 (t, J=7.3 Hz, 1H), 7.32 (m, 4H), 7.23 (m, 1H), 4.85 (m, 1H), 1.39 (d, J=7.0 Hz, 3H). Example 53 was prepared according to Scheme 3 method A following similar procedures described for Example 52, which can be achieved by those of ordinary skill in the art of organic synthesis.

Workup

  1. custompurified by mass-triggered reverse-phase HPLC
  2. additionThe fractions containing pure product
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b57dea506fa941fab3c0b1d4c47c5b7c
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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