O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → 3-chloro-N-[(1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethyl]-4-(5-methyl-morpholin-3-on-4-yl)-benzamide

HRID 551261Notes

Reaction equation

HRID 551261 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[CH:16]([CH3:17])[CH2:15][O:14][CH2:13][C:12]1=[O:18])[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>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[CH:16]([CH3:17])[CH2:15][O:14][CH2:13][C:12]1=[O:18])[C:5]([NH:31][C@H:27]([C:25]1[NH:24][C:23]2[CH:32]=[CH:33][C:20]([Cl:19])=[CH:21][C:22]=2[N:26]=1)[CH2:28][O:29][CH3:30])=[O:7]

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 670485053-Chloro-4-(5-methyl-morpholin-3-on-4-yl)-benzoic acidHCID 178495727HCID 178495727, compound

Product 1

HCID 1784957463-chloro-N-[(1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethyl]-4-(5-methyl-morpholin-3-on-4-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared analogously to Example 1f from 3-chloro-4-(5-methyl-morpholin-3-on-4-yl)-benzoic acid and (1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethylamine with TBTU and TEA in DMF.

Sources & evidence

ORD record
ord-b1b169029f1342f8be7ec5f674ab08b6
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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