Reaction #44040

ord-29229ebb900347458e26b79b02416943

Reaction equation

O=C1CCN(S(=O)(=O)c2ccc(Cl)cc2)C(c2cncnc2)C1
compound 71
O=C1CCN(S(=O)(=O)c2ccc(Cl)cc2)C(c2cncnc2)C1
1-(4-chlorophenylsulfonyl)-2-(pyrimidin-5-yl)piperidin-4-one
C[C@H]1CC(=O)C[C@H](C)N1S(=O)(=O)c1ccc(Cl)cc1
trans-1-(4-Chlorophenylsulfonyl)-2,6-dimethylpiperidin-4-one
C[C@H]1CC(=O)C[C@H](C)N1S(=O)(=O)c1ccc(Cl)cc1
trans-1-(4-chlorophenylsulfonyl)-2,6-dimethylpiperidin-4-one
COC(OC)N(C)C
DMF-DMA
NN.O
hydrazine hydrate
→
C[C@H]1Cc2[nH]ncc2[C@H](C)N1S(=O)(=O)c1ccc(Cl)cc1
trans-5-(4-Chlorophenylsulfonyl)-4,6-dimethyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine

Reactants

O=C1CCN(S(=O)(=O)c2ccc(Cl)cc2)C(c2cncnc2)C1
compound 71
O=C1CCN(S(=O)(=O)c2ccc(Cl)cc2)C(c2cncnc2)C1
1-(4-chlorophenylsulfonyl)-2-(pyrimidin-5-yl)piperidin-4-one
C[C@H]1CC(=O)C[C@H](C)N1S(=O)(=O)c1ccc(Cl)cc1
trans-1-(4-Chlorophenylsulfonyl)-2,6-dimethylpiperidin-4-one
C[C@H]1CC(=O)C[C@H](C)N1S(=O)(=O)c1ccc(Cl)cc1
trans-1-(4-chlorophenylsulfonyl)-2,6-dimethylpiperidin-4-one
COC(OC)N(C)C
DMF-DMA
NN.O
hydrazine hydrate

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

trans-1-(4-Chlorophenylsulfonyl)-2,6-dimethylpiperidin-4-one (94) was treated with DMF-DMA followed by hydrazine hydrate as described for compound 71 in Example 4. 1H-NMR (CD3OD) δ 7.81-7.79 (m, 2H), 7.62 (m, 3H), 5.38 (q, J=7.1 Hz, 1H), 4.20-4.13, (m, 1H), 2.78 (dd, J=16.2, 4.4 Hz, 1H), 2.56-2.48 (m, 1H), 1.54-1.47 (m, 6H); MS (m/z) 326.0 (M+H)+.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07732609B2uspto-grants-2010_06