10-bromo-N3-tetrahydropyran-4-yl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2,3-dicarboxamide → 10-[2-[(3R)-3-hydroxy-1-methyl-2-oxo-3-piperidyl]ethynyl]-N3-tetrahydropyran-4-yl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2,3-dicarboxamide

HRID 575364Notes

Reaction equation

HRID 575364 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([C:18]([NH:20][CH:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[O:19])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:27]=1.[C:28]([C@:30]1([OH:38])[CH2:35][CH2:34][CH2:33][N:32]([CH3:36])[C:31]1=[O:37])#[CH:29]>>[OH:38][C@@:30]1([C:28]#[C:29][C:2]2[CH:3]=[CH:4][C:5]3[O:11][CH2:10][CH2:9][N:8]4[C:12]([C:18]([NH:20][CH:21]5[CH2:22][CH2:23][O:24][CH2:25][CH2:26]5)=[O:19])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]4[C:6]=3[CH:27]=2)[CH2:35][CH2:34][CH2:33][N:32]([CH3:36])[C:31]1=[O:37]

Participants

3

Reactant 2

HCID 8669330310-bromo-N3-tetrahydropyran-4-yl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2,3-dicarboxamideHCID 86693406(3R)-3-ethynyl-3-hydroxy-1-methylpiperidin-2-one

Product 1

HCID 8669340510-[2-[(3R)-3-hydroxy-1-methyl-2-oxo-3-piperidyl]ethynyl]-N3-tetrahydropyran-4-yl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2,3-dicarboxamideYield 25.3%

Procedure

10-bromo-N3-tetrahydropyran-4-yl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2,3-dicarboxamide was reacted with (3R)-3-ethynyl-3-hydroxy-1-methyl-piperidin-2-one similarly to as described in General Procedure F with non-critical modifications to afford 22 mg (25.3%) of 10-[2-[(3R)-3-hydroxy-1-methyl-2-oxo-3-piperidyl]ethynyl]-N3-tetrahydropyran-4-yl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2,3-dicarboxamide.

Sources & evidence

ORD record
ord-f050d002deb44a7ba359b8a53191ad5b
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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