Oxolan-3-yl methanesulfonate → HCID 56942362, compound

HRID 1046497Notes

Reaction equation

HRID 1046497 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9]([C:31]3[CH:32]=[N:33][NH:34][CH:35]=3)=[N:10][N:11](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:7]=2[CH:6]=[CH:5][N:4]=1.CS(O[CH:41]1[CH2:45][CH2:44][O:43][CH2:42]1)(=O)=O>>[O:43]1[CH2:44][CH2:45][CH:1]([O:2][C:3]2[C:8]3[C:9]([C:31]4[CH:35]=[N:34][N:33]([CH:45]5[CH2:41][CH2:42][O:43][CH2:44]5)[CH:32]=4)=[N:10][NH:11][C:7]=3[CH:6]=[CH:5][N:4]=2)[CH2:41][CH2:42]1

Participants

3

Reactant 2

HCID 15278452Oxolan-3-yl methanesulfonateHCID 136352321HCID 136352321, compound

Product 1

HCID 56942362HCID 56942362, compoundYield 24%

Procedure

Prepared according to the general procedure described in Example 92, by reacting 4-methoxy-3-(1H-pyrazol-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridine with tetrahydrofuran-3-yl methanesulfonate to give the title compound as a mixture of enantiomers. The enantiomers were separated via supercritical fluid chromatography to give the separated enantiomers. (7.9 mg, 7.7 mg, total yield 24% over two steps). LC-MS (Method G): m/z=286.1 [M+H]+; 2.97 min. 1H-NMR (400 MHz, DMSO): δ 13.27 (s, 1H), 8.32 (s, 1H), 8.04 (s, 1H), 7.85 (d, J=6.0, 1H), 7.09 (d, J=6.0 1H), 5.17-5.09 (m, 1H), 4.06 (s, 3H), 4.05-3.98 (m, 2H), 3.95 (dd, J=9.4, J=3.7, 1H), 3.91-3.83 (m, 1H), 2.47-2.36 (m, 1H), 2.36-2.25 (m, 1H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-de88117437584119afc15b2e2d9fa3c2
Source dataset
uspto-grants-2013_10
Patent number
US08569281B2

Reaction notes

Loading…