Trifluoroacetic acid → 1-[(1R)-2-methoxy-1-phenylethyl]-3-[3-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl]urea

HRID 571425Notes

Reaction equation

HRID 571425 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]([NH:11][C:12]([NH:14][C:15]1[N:20]=[CH:19][C:18]2[C:21]([C:43]3[CH:44]=[N:45][N:46]([CH3:48])[CH:47]=3)=[N:22][N:23](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:17]=2[CH:16]=1)=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[CH3:1][O:2][CH2:3][C@H:4]([NH:11][C:12]([NH:14][C:15]1[N:20]=[CH:19][C:18]2[C:21]([C:43]3[CH:44]=[N:45][N:46]([CH3:48])[CH:47]=3)=[N:22][NH:23][C:17]=2[CH:16]=1)=[O:13])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 89525815(S)-1-(2-methoxy-1-phenylethyl)-3-(3-(1-methyl-1H-pyrazol-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)urea

Product 1

HCID 895360651-[(1R)-2-methoxy-1-phenylethyl]-3-[3-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl]ureaYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of (S)-1-(2-methoxy-1-phenylethyl)-3-(3-(1-methyl-1H-pyrazol-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)urea (63.4 mg, 0.100 mmol) and trifluoroacetic acid (0.383 ml, 5.00 mmol) in Dichloromethane (2.0 ml) was added triethylsilane (17.45 mg, 0.150 mmol). The resulting mixture was allowed to stir at rt for 18 h. LC-MS showed the completion of the reaction. After concentration the residue was purified by reverse phase HPLC to provide desired product (17.3 mg, 0.028 mmol, 27.9% yield). MS ESI Calc'd for C20H21N7O2 [M+H]+ 392, found 392

Workup

  1. customthe completion of the reaction
  2. concentrationAfter concentration the residue
  3. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-5c88136a63cc482abb213a880a94bdf5
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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