Chlorine → HCID 178427143, compound

HRID 2054019Notes

Reaction equation

HRID 2054019 reaction equation
[F:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=2[CH3:18])=[O:8])[CH2:3]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[Cl:50][C:51]1[CH:62]=[CH:61][C:54]2[NH:55][C:56]([C@@H:58]([NH2:60])[CH3:59])=[N:57][C:53]=2[CH:52]=1.ClCl>O1CCCC1.ClCCl.C(O)C>[Cl:50][C:51]1[CH:62]=[CH:61][C:54]2[NH:55][C:56]([C@@H:58]([NH:60][C:13](=[O:15])[C:12]3[CH:16]=[CH:17][C:9]([C:7]([N:4]4[CH2:5][CH2:6][CH:2]([F:1])[CH2:3]4)=[O:8])=[C:10]([CH3:18])[CH:11]=3)[CH3:59])=[N:57][C:53]=2[CH:52]=1

Participants

8

Reactant 5

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 42034613(S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamineHCID 69309871HCID 69309871, compound

Product 1

HCID 178427143HCID 178427143, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from rac.-4-(3-fluoropyrrolidin-1-ylcarbonyl)-3-methylbenzoic acid, TBTU, diisopropylethylamine and (1S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine in tetrahydrofuran. Yield: 49%; Rf value: 0.30 (silica gel: dichloromethane/ethanol=9:1); C22H22ClFN4O2 (428.893); mass spectrum: (M+H)+=429/431 (chlorine isotope).

Sources & evidence

ORD record
ord-0d08152f6ab94078bc5db616f8b4666b
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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