Trifluoroacetic acid → HCID 118271929, compound

HRID 590813Notes

Reaction equation

HRID 590813 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[C:16]2[CH:17]=[N:18][C:19]([NH:21][C:22]([NH:24][C@@H:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])=[O:23])=[CH:20][C:15]=2[N:14](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:13]=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)Cl>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[C:16]2[CH:17]=[N:18][C:19]([NH:21][C:22]([NH:24][C@@H:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])=[O:23])=[CH:20][C:15]=2[NH:14][N:13]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 118271799HCID 118271799, compound

Product 1

HCID 118271929HCID 118271929, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-1-(3-(1,3-Dioxoisoindolin-2-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (229 mg, 0.342 mmol) was dissolved in DCM (2 mL), charged with TFA (660 μL, 8.56 mmol) and triethylsilane (54.7 μL, 0.342 mmol), and stirred at room temperature for 30 min. The solvents were concentrated in vacuo and the residue was treated with triethylamine (1 mL). Purification via flash chromotagraphy (10-100% EtOAc/DCM) afforded (R)-1-(3-(1,3-dioxoisoindolin-2-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. MS ESI calc'd. for C23H18N6O3 [M+1]+ 427. found 427.

Workup

  1. concentrationThe solvents were concentrated in vacuo
  2. additionthe residue was treated with triethylamine (1 mL)
  3. customPurification via flash chromotagraphy (10-100% EtOAc/DCM)

Sources & evidence

ORD record
ord-14971a3ae01c4b009957da5565d4017d
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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