Hydrazine hydrate (1:1) → HCID 68498053, compound

HRID 15762Notes

Reaction equation

HRID 15762 reaction equation
Cl[C:2]1C=CC(S(N2[C@@H](C)CC(=O)C[C@@H]2C)(=O)=O)=CC=1.CN(C(OC)OC)C.O.NN.[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([S:38]([N:41]2[CH2:46][CH2:45]C(=O)[CH2:43][CH:42]2[C:48]2[CH:49]=[N:50]C=[N:52][CH:53]=2)(=[O:40])=[O:39])=[CH:34][CH:33]=1>>[Cl:31][C:32]1[CH:33]=[CH:34][C:35]([S:38]([N:41]2[C@@H:46]([CH3:45])[CH2:2][C:53]3[NH:52][N:50]=[CH:49][C:48]=3[C@@H:42]2[CH3:43])(=[O:39])=[O:40])=[CH:36][CH:37]=1

Participants

5

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 593423911-(4-Chlorophenylsulfonyl)-2-(pyrimidin-5-yl)piperidin-4-oneHCID 68500265HCID 68500265, compound

Product 1

HCID 68498053HCID 68498053, compound

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)+.

Sources & evidence

ORD record
ord-29229ebb900347458e26b79b02416943
Source dataset
uspto-grants-2010_06
Patent number
US07732609B2

Reaction notes

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