2-Chlorophenol → (R)-3-((2-chlorophenoxy)methyl)-10-(3-hydroxy-3-(5-methylisoxazol-3-yl)but-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575270Notes

Reaction equation

HRID 575270 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH2:18]N4C5C=CC=CC=5N=C4C)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:29]=1.[Cl:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[OH:37].[CH3:38][C:39]1[O:43][N:42]=[C:41]([C@:44]([OH:48])([C:46]#[CH:47])[CH3:45])[CH:40]=1>CS(C)=O.BrC1C=CC2OCCN3C(COC4C=CC=CC=4Cl)=C(C(N)=O)N=C3C=2C=1.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:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[O:37][CH2:18][C:12]1[N:8]2[CH2:9][CH2:10][O:11][C:5]3[CH:4]=[CH:3][C:2]([C:47]#[C:46][C@@:44]([OH:48])([C:41]4[CH:40]=[C:39]([CH3:38])[O:43][N:42]=4)[CH3:45])=[CH:29][C:6]=3[C:7]2=[N:14][C:13]=1[C:15]([NH2:17])=[O:16]

Participants

7

Reactant 3

HCID 72452-ChlorophenolHCID 58221468(R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-olHCID 8669328810-bromo-3((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 86693297(R)-3-((2-chlorophenoxy)methyl)-10-(3-hydroxy-3-(5-methylisoxazol-3-yl)but-1-yn-1-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 28%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 679Dimethyl SulfoxideSolventHCID 8669329810-Bromo-3-((2-chlorophenoxy)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideSolvent

Procedure

Similar to as 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 (prepared similarly to 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 replacing 2-methylbenzimidazole with 2-chlorophenol) was reacted with (R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-ol to give the titled compound as a colorless solid (39 mg, 28%).

Sources & evidence

ORD record
ord-24bb4483289b4c1abe1095909d75ae60
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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