HCID 68442799, compound → HCID 57520099, compound

HRID 331775Notes

Reaction equation

Br[C:2]1[C:3]([O:14][CH2:15][C:16]2[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:18][O:19][C:20]=2[CH3:21])=[N:4][CH:5]=[C:6]([CH:13]=1)[C:7]([NH:9][CH:10]([CH3:12])[CH3:11])=[O:8].Br[C:29]1C(OCC2C(C3C=CC=CC=3)=NOC=2C)=NC=C(C=1)C(NC1CCOCC1)=O>>[CH:10]([NH:9][C:7](=[O:8])[C:6]1[CH:13]=[C:2]([CH3:29])[C:3]([O:14][CH2:15][C:16]2[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:18][O:19][C:20]=2[CH3:21])=[N:4][CH:5]=1)([CH3:12])[CH3:11]

Participants

Reactant 2

HCID 68442799HCID 68442799, compound

HCID 68445038HCID 68445038, compound

Product 1

HCID 57520099HCID 57520099, compoundYield 52%

Procedure

As described for example 66, 5-bromo-N-isopropyl-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinamide (150 mg, 0.35 mmol), instead of 5-bromo-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-(tetrahydro-pyran-4-yl)-nicotinamide was converted to the title compound (73 mg, 52%) which was obtained as an off white gum. MS: m/e=366.0 [M+H]+.

Sources & evidence

ORD record: ord-aa386f4e2c534270a478652ff69d336b
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877782B2

Reaction notes

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