4-Methylmorpholine → HCID 178523887, compound

HRID 2053914Notes

Reaction equation

HRID 2053914 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([N:13]1[CH2:17][CH:16]=[CH:15][CH2:14]1)=[O:12])[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.[Cl:47][C:48]1[CH:60]=[CH:59][C:51]2[NH:52][C:53]([C@@H:55]([NH2:58])[CH2:56][OH:57])=[N:54][C:50]=2[CH:49]=1.ClCl>CN(C)C=O.ClCCl.CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([N:13]1[CH2:17][CH:16]=[CH:15][CH2:14]1)=[O:12])[C:5]([NH:58][C@H:55]([C:53]1[NH:52][C:51]2[CH:59]=[CH:60][C:48]([Cl:47])=[CH:49][C:50]=2[N:54]=1)[CH2:56][OH:57])=[O:7]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 24526Chlorine2×HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 693151643-Chloro-4-(2,5-dihydropyrrol-1-ylcarbonyl)benzoic acidHCID 178511833HCID 178511833, compound

Product 1

HCID 178523887HCID 178523887, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 1g from 3-chloro-4-(2,5-dihydropyrrol-1-ylcarbonyl)benzoic acid, TBTU, N-methylmorpholine, and (1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-hydroxyethylamine in N,N-dimethylformamide. Yield: 20%; Rf value: 0.6 (silica gel; dichloromethane/methanol=95:5); C21H18Cl2N4O3 (445.31); mass spectrum: (M+H)+=445/447/449 (chlorine isotope) and (M+H)−=443/445/447 (chlorine isotope).

Sources & evidence

ORD record
ord-87bec47cf32d4784aa5b1a2d0276864b
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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