6-Methoxypyridazin-3-amine → 8-Benzenesulfonyl-2-(6-methoxy-pyridazin-3-yl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 2194011Notes

Reaction equation

HRID 2194011 reaction equation
C([O:3][C:4]([C:6]1([CH2:21][CH2:22]OC)[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:8][CH2:7]1)=O)C.[Cl-].C[Al+]C.[NH2:29][C:30]1[N:31]=[N:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=1>CCCCCCC>[C:15]1([S:12]([N:9]2[CH2:8][CH2:7][C:6]3([C:4](=[O:3])[N:29]([C:30]4[N:31]=[N:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=4)[CH2:22][CH2:21]3)[CH2:11][CH2:10]2)(=[O:13])=[O:14])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 816736-Methoxypyridazin-3-amineHCID 16686359Dimethylalumanylium chlorideHCID 667870971-Benzenesulfonyl-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

Product 1

HCID 498019628-Benzenesulfonyl-2-(6-methoxy-pyridazin-3-yl)-2,8-diaza-spiro[4.5]decan-1-oneYield 14.1%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

This material was prepared in analogy to example 1 step D) from 1-Benzenesulfonyl-4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester (0.15 g), dimethylaluminium chloride in heptane (0.9 molar, 0.71 ml) and 3-amino-6-methoxypyridazine (0.069 g) to give the desired 8-benzenesulfonyl-2-(6-methoxy-pyridazin-3-yl)-2,8-diaza-spiro[4.5]decan-1-one (0.024 g) as a white solid. MS (ESI): 403.146 (MH+).

Sources & evidence

ORD record
ord-0965a8fb450c41cd9036043bc7d5d5a2
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

Loading…