Chlorine → HCID 178448329, compound

HRID 2054040Notes

Reaction equation

HRID 2054040 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[C:12]([NH:14][C@H:15]([C:19]1[NH:23][C:22]2[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:21]=2[N:20]=1)[CH2:16][CH2:17][CH3:18])=[O:13])[C:6](O)=[O:7].CN(C(O[N:39]1N=NC2C=[CH:43][CH:44]=[CH:45][C:40]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.N1CC=CC1.ClCl>O1CCCC1.ClCCl.C(O)C>[Cl:28][C:26]1[CH:25]=[CH:24][C:22]2[NH:23][C:19]([C@@H:15]([NH:14][C:12](=[O:13])[C:11]3[CH:10]=[CH:9][C:5]([C:6]([N:39]4[CH2:40][CH:45]=[CH:44][CH2:43]4)=[O:7])=[CH:4][C:3]=3[C:2]([F:1])([F:29])[F:30])[CH2:16][CH2:17][CH3:18])=[N:20][C:21]=2[CH:27]=1

Participants

8

Reactant 5

HCID 24526ChlorineHCID 660593-PyrrolineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178448337HCID 178448337, compound

Product 1

HCID 178448329HCID 178448329, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from (1S)-3-trifluoromethyl-4-{N-[1-(5-chloro-1H-benzimidazol-2-yl)butyl]aminocarbonyl}benzoic acid, TBTU, diisopropylethylamine, and 3-pyrroline in tetrahydrofuran. Yield: 64%; Rf value: 0.47 (silica gel: dichloromethane/ethanol=9:1); C24H22ClF3N4O2 (490.911); mass spectrum: (M+H)+=491/493 (chlorine isotope).

Sources & evidence

ORD record
ord-f1f336fde4f54799bf2c4ea04deb31f7
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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