Trifluoroacetic acid → (S)-1-((1-hydroxycyclobutyl)(phenyl)methyl)-3-(3-(2-methoxyethoxy)-1H-pyrazolo[4,3-c]pyridin-6-yl)urea
Reaction equation
[OH:1][C:2]1([C@H:6]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[NH:7][C:8]([NH:10][C:11]2[N:16]=[CH:15][C:14]3[C:17]([O:39][CH2:40][CH2:41][O:42][CH3:43])=[N:18][N:19](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:13]=3[CH:12]=2)=[O:9])[CH2:5][CH2:4][CH2:3]1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)Cl>[OH:1][C:2]1([C@H:6]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[NH:7][C:8]([NH:10][C:11]2[N:16]=[CH:15][C:14]3[C:17]([O:39][CH2:40][CH2:41][O:42][CH3:43])=[N:18][NH:19][C:13]=3[CH:12]=2)=[O:9])[CH2:3][CH2:4][CH2:5]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In a manner similar to that described previously (e.g. Example 40, Step 3), (S)-1-((1-hydroxycyclobutyl)(phenyl)-methyl)-3-(3-(2-methoxyethoxy)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)urea was treated with TFA and triethylsilane in DCM. The product (102) was purified by Reverse phase C-18 HPLC (eluting with Acetonitrile/Water+0.1% TFA). MS: [M+H]+ m/z 412. 1H NMR (500 MHz, DMSO) δ 12.24 (s, 1H), 9.48 (s, 1H), 8.61 (s, 1H), 7.85 (bs, 1H), 7.38 (t, 2H, J=7.5 Hz), 7.36 (s, 1H), 7.27 (t, 2H, J=7.5 Hz), 7.20 (t, 2H, J=7.5 Hz), 4.78 (d, 1H, J=9 Hz), 4.42 (t, 2H, J=4.5 Hz), 3.70 (t, 2H, J=4.5 Hz), 3.30 (s, 3H), 2.12 (1H, m), 2.00 (m, 2H), 1.79 (m, 1H), 1.69 (m, 1H), 1.59 (m, 1H).
Workup
- customThe product (102) was purified by Reverse phase C-18 HPLC (eluting with Acetonitrile/Water+0.1% TFA)
Sources & evidence
- ORD record
- ord-bba5124b288d4045b601200e859b6794
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09226922B2
Reaction notes
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