(R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-ol → (R)-9-(3-hydroxy-3-(5-methylisoxazol-3-yl)but-1-yn-1-yl)-N3-methyl-4,5-dihydrobenzo[b]pyrazolo [1,5-d][1,4]oxazepine-2,3-dicarboxamide

HRID 575305Notes

Reaction equation

HRID 575305 reaction equation
Br[C:2]1[CH:22]=[CH:21][C:5]2[O:6][CH2:7][CH2:8][C:9]3[N:10]([N:11]=[C:12]([C:18]([NH2:20])=[O:19])[C:13]=3[C:14]([NH:16][CH3:17])=[O:15])[C:4]=2[CH:3]=1.[CH3:23][C:24]1[O:28][N:27]=[C:26]([C@:29]([OH:33])([C:31]#[CH:32])[CH3:30])[CH:25]=1>>[OH:33][C@:29]([C:26]1[CH:25]=[C:24]([CH3:23])[O:28][N:27]=1)([CH3:30])[C:31]#[C:32][C:2]1[CH:22]=[CH:21][C:5]2[O:6][CH2:7][CH2:8][C:9]3[N:10]([N:11]=[C:12]([C:18]([NH2:20])=[O:19])[C:13]=3[C:14]([NH:16][CH3:17])=[O:15])[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 58221468(R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-olHCID 866933369-bromo-N3-methyl-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepine-2,3-dicarboxamide

Product 1

HCID 86693337(R)-9-(3-hydroxy-3-(5-methylisoxazol-3-yl)but-1-yn-1-yl)-N3-methyl-4,5-dihydrobenzo[b]pyrazolo [1,5-d][1,4]oxazepine-2,3-dicarboxamideYield 26%

Procedure

Similar to as described in General Procedure G, 9-bromo-N3-methyl-4,5-dihydrobenzo[b]pyrazolo[1,5-d][1,4]oxazepine-2,3-dicarboxamide was reacted with (R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-ol to give the titled compound as an off-white solid (37 mg, 26%).

Sources & evidence

ORD record
ord-e9d331dd018946c6a517cde291dbba07
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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