Isobutane → tert-Butyl 4-(3-carbamoyl-1-(4-cyano-3-fluorophenyl)-6-oxo-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylate

HRID 386567

Reaction equation

HRID 386567 reaction equation
CS(C1C=CC([N:11]2C(=O)C=CC(C([O-])=O)=N2)=CC=1)(=O)=O.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][CH:31]([O:34][C:35]2[C:36]([C:51]([O:53]C)=O)=[N:37][N:38]([C:42]3[CH:47]=[CH:46][C:45]([C:48]#[N:49])=[C:44]([F:50])[CH:43]=3)[C:39](=[O:41])[CH:40]=2)[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].C(C)(C)C>>[C:51]([C:36]1[C:35]([O:34][CH:31]2[CH2:32][CH2:33][N:28]([C:26]([O:25][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:27])[CH2:29][CH2:30]2)=[CH:40][C:39](=[O:41])[N:38]([C:42]2[CH:47]=[CH:46][C:45]([C:48]#[N:49])=[C:44]([F:50])[CH:43]=2)[N:37]=1)(=[O:53])[NH2:11]

Participants

4

Reactant 3

HCID 6360IsobutaneHCID 44620996Methyl 4-(1-(tert-butoxycarbonyl)piperidin-4-yloxy)-1-(4-cyano-3-fluorophenyl)-6-oxo-1,6-dihydropyridazine-3-carboxylateHCID 866586581-(4-(Methylsulfonyl)phenyl)-6-oxo-1,6-dihydropyridazine-3-carboxylate

Product 1

HCID 67445416tert-Butyl 4-(3-carbamoyl-1-(4-cyano-3-fluorophenyl)-6-oxo-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylateYield 91%

Procedure

tert-Butyl 4-(3-carbamoyl-1-(4-cyano-3-fluorophenyl)-6-oxo-1,6-dihydropyridazin-4-yloxy)piperidine-1-carboxylate was prepared in 91% yield according to procedures described in Example 31 (Step A) substituting methyl 441-(tert-butoxycarbonyl)piperidin-4-yloxy)-1-(4-(methylsulfonyl)phenyl)-6-oxo-1,6-dihydropyridazine-3-carboxylate for methyl 4-(1-(tert-butoxycarbonyl)piperidin-4-yloxy)-1-(4-cyano-3-fluorophenyl)-6-oxo-1,6-dihydropyridazine-3-carboxylate (example 29). MS (ESI) 402 (M+H-tBu).

Sources & evidence

ORD record
ord-b3d7758759f2471b81a8c11237c59839
Source dataset
uspto-grants-2013_02
Patent number
US08372837B2

Linked notes

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