5-Bromo-2-(tetrahydro-2H-pyran-4-yloxy)pyridine → Rac-[1-(3,4-dichloro-phenyl)-2-oxo-2-[6-(tetrahydro-pyran-4-yloxy)-pyridin-3-yl]-ethyl]-carbamic acid tert-butyl ester

HRID 384918Notes

Reaction equation

HRID 384918 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)[C:9](=[O:14])N(OC)C)([CH3:4])([CH3:3])[CH3:2].Br[C:25]1[CH:26]=[CH:27][C:28]([O:31][CH:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[N:29][CH:30]=1>>[C:1]([O:5][C:6](=[O:23])[NH:7][CH:8]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=1)[C:9](=[O:14])[C:25]1[CH:30]=[N:29][C:28]([O:31][CH:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[CH:27][CH:26]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 219143915-Bromo-2-(tetrahydro-2H-pyran-4-yloxy)pyridine2×HCID 87442373Rac-[(3,4-dichloro-phenyl)-(methoxy-methyl-carbamoyl)-methyl]-carbamic acid tert-butyl ester2×

Product 1

HCID 68410413Rac-[1-(3,4-dichloro-phenyl)-2-oxo-2-[6-(tetrahydro-pyran-4-yloxy)-pyridin-3-yl]-ethyl]-carbamic acid tert-butyl ester

Procedure

The title compound was prepared from rac-[(3,4-dichloro-phenyl)-(methoxy-methyl-carbamoyl)-methyl]-carbamic acid tert-butyl ester (Intermediate 9) and 5-bromo-2-(tetrahydro-pyran-4-yloxy)-pyridine (Intermediate 20) in analogy to Example 1a): MS (ISN): 479.1 and 481.2 (M−H)−.

Sources & evidence

ORD record
ord-6bc7947561304a489386f7b20315f3c1
Source dataset
uspto-grants-2013_02
Patent number
US08367838B2

Reaction notes

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