4-Methylmorpholine → HCID 178428633, compound

HRID 2053782Notes

Reaction equation

HRID 2053782 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7]([CH2:9][C:10]([OH:12])=O)=[N:8][C:4]=2[CH:3]=1.CN(C(ON1N=[N:30][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C[N:38]1[CH2:43][CH2:42]O[CH2:40][CH2:39]1.ClCl.ClCCl.[CH2:49]([OH:51])[CH3:50]>CN(C)C=O>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7]([CH2:9][C:10]([NH:30][C:25]3[CH:24]=[CH:29][C:50]([C:49]([N:38]4[CH2:43][CH2:42][CH2:40][CH2:39]4)=[O:51])=[C:27]([CH3:28])[CH:26]=3)=[O:12])=[N:8][C:4]=2[CH:3]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 24526ChlorineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21584144Dichloromethane ethanolHCID 178525236HCID 178525236, compound

Product 1

HCID 178428633HCID 178428633, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared analogously to Example 1g from (5-chloro-1H-benzimidazol-2-yl)acetic acid, TBTU, N-methylmorpholine, and 4-amino-2-methylbenzoic acid pyrrolidine amide in N,N-dimethylformamide and subsequent chromatography on silica gel (gradient: dichloromethane/ethanol=100:0□25:1□19:1□19:1); Yield: 14 mg (7.1%); Rf value: 0.45 (silica gel; dichloromethane/ethanol=9:1); C21H21ClN4O2 (396.88); mass spectrum: (M−H)-=395/397 (chlorine isotope).

Sources & evidence

ORD record
ord-12b46fb259ed435eb930a509f1a859b3
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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