(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one → (R)-3-((2-chlorophenoxy)methyl)-10-((3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl)ethynyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575271Notes

Reaction equation

HRID 575271 reaction equation
[C:1]([C@:3]1([OH:10])[CH2:7][CH2:6][N:5]([CH3:8])[C:4]1=[O:9])#[CH:2].Br[C:12]1[CH:13]=[CH:14][C:15]2[O:21][CH2:20][CH2:19][N:18]3[C:22]([CH2:28][O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[Cl:36])=[C:23]([C:25]([NH2:27])=[O:26])[N:24]=[C:17]3[C:16]=2[CH:37]=1>CS(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:36][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=1[O:29][CH2:28][C:22]1[N:18]2[CH2:19][CH2:20][O:21][C:15]3[CH:14]=[CH:13][C:12]([C:2]#[C:1][C@:3]4([OH:10])[CH2:7][CH2:6][N:5]([CH3:8])[C:4]4=[O:9])=[CH:37][C:16]=3[C:17]2=[N:24][C:23]=1[C:25]([NH2:27])=[O:26]

Participants

5

Reactant 2

HCID 86693296(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-oneHCID 8669329810-Bromo-3-((2-chlorophenoxy)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 86693299(R)-3-((2-chlorophenoxy)methyl)-10-((3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl)ethynyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 23%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

Similar to as described in General Procedure E with the exceptions of using Pd(PPh3)4 in DMSO, 10-bromo-3-((2-chlorophenoxy)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide was reacted with (R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one to give the titled compound as a colorless solid (12 mg, 23%).

Sources & evidence

ORD record
ord-52bca7a5e40f498c95f68d90ec65cf0c
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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