4-Methylmorpholine → HCID 178427147, compound

HRID 551196Notes

Reaction equation

HRID 551196 reaction equation
[O:1]=[S:2]1(=[O:17])[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][C:8]=1[CH3:16].[Cl:18][C:19]1[CH:30]=[CH:29][C:22]2[NH:23][C:24]([C@@H:26]([NH2:28])[CH3:27])=[N:25][C:21]=2[CH:20]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1>CN(C=O)C.C(OCC)(=O)C>[Cl:18][C:19]1[CH:30]=[CH:29][C:22]2[NH:23][C:24]([C@@H:26]([NH:28][C:11](=[O:13])[C:10]3[CH:14]=[CH:15][C:7]([N:3]4[CH2:4][CH2:5][CH2:6][S:2]4(=[O:1])=[O:17])=[C:8]([CH3:16])[CH:9]=3)[CH3:27])=[N:25][C:21]=2[CH:20]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 246888114-(1,1-Dioxo-1,2-thiazolidin-2-yl)-3-methylbenzoic acidHCID 42034613(S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine

Product 1

HCID 178427147HCID 178427147, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Prepared analogously to Example 1f from 4-(1,1-dioxo-isothiazolidin-2-yl)-3-methyl-benzoic acid, (1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamine, TBTU and NMM in DMF with subsequent extraction with ethyl acetate, drying over magnesium sulphate, activated charcoal and silica gel followed by purification on silica gel (eluant: dichloromethane/isopropanol 95:5).

Workup

  1. dry with materialdrying over magnesium sulphate, activated charcoal and silica gel
  2. customfollowed by purification on silica gel (eluant: dichloromethane/isopropanol 95:5)

Sources & evidence

ORD record
ord-2128921ac95146e5a2d0d33f589fdd80
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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