4-Methylmorpholine → N-[(1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethyl]-3-methyl-4-(5-oxo-[1,4]oxazepan-4-yl)-benzamide

HRID 551235Notes

Reaction equation

HRID 551235 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[C:17](=[O:18])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)[C:5]([OH:7])=O.[Cl:19][C:20]1[CH:33]=[CH:32][C:23]2[NH:24][C:25]([C@@H:27]([NH2:31])[CH2:28][O:29][CH3:30])=[N:26][C:22]=2[CH:21]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[Cl:19][C:20]1[CH:33]=[CH:32][C:23]2[NH:24][C:25]([C@@H:27]([NH:31][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][C:10]([N:11]4[C:17](=[O:18])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]4)=[C:2]([CH3:1])[CH:3]=3)[CH2:28][O:29][CH3:30])=[N:26][C:22]=2[CH:21]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 670483253-Methyl-4-(5-oxo-[1,4]oxazepan-4-yl)benzoic acidHCID 178495727HCID 178495727, compound

Product 1

HCID 178495745N-[(1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethyl]-3-methyl-4-(5-oxo-[1,4]oxazepan-4-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared analogously to Example 1f from 3-methyl-4-(5-oxo-[1,4]oxazepan-4-yl)benzoic acid, (1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethylamine, TBTU and NMM in DMF with subsequent purification by preparative HPLC.

Sources & evidence

ORD record
ord-764eebb67f954c939bf2622a9547806c
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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