10-bromo-3((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide → (R)-10-((3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl)ethynyl)-3-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575269

Reaction equation

HRID 575269 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][N:29]4[C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=5[N:31]=[C:30]4[CH3:38])=[C:23]([C:25]([NH2:27])=[O:26])[N:24]=[C:17]3[C:16]=2[CH:39]=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>[OH:10][C@@:3]1([C:1]#[C:2][C:12]2[CH:13]=[CH:14][C:15]3[O:21][CH2:20][CH2:19][N:18]4[C:22]([CH2:28][N:29]5[C:33]6[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=6[N:31]=[C:30]5[CH3:38])=[C:23]([C:25]([NH2:27])=[O:26])[N:24]=[C:17]4[C:16]=3[CH:39]=2)[CH2:7][CH2:6][N:5]([CH3:8])[C:4]1=[O:9]

Participants

5

Reactant 2

HCID 8669328810-bromo-3((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 86693296(R)-3-ethynyl-3-hydroxy-1-methylpyrrolidin-2-one

Product 1

HCID 86693295(R)-10-((3-hydroxy-1-methyl-2-oxopyrrolidin-3-yl)ethynyl)-3-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 19%

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-methyl-1H-benzo[d]imidazol-1-yl)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 yield the titled compound as a yellow solid (21 mg, 19%).

Sources & evidence

ORD record
ord-5196f80411df498c84b7d4b2984b16a9
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Linked notes

Loading…