Chlorine → HCID 178462057, compound

HRID 2054036Notes

Reaction equation

HRID 2054036 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:11]=[C:10]([C:12]([NH:14][C@H:15]([C:17]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:19]=3[N:18]=2)[CH3:16])=[O:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.CN(C(O[N:37]1N=NC2C=[CH:41][CH:42]=[CH:43][C:38]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:26][C:24]1[CH:23]=[CH:22][C:20]2[NH:21][C:17]([C@@H:15]([NH:14][C:12](=[O:13])[C:10]3[CH:9]=[CH:8][C:4]([C:5]([N:37]4[CH2:38][CH:43]=[CH:42][CH2:41]4)=[O:7])=[C:3]([C:2]([F:28])([F:1])[F:27])[CH:11]=3)[CH3:16])=[N:18][C:19]=2[CH:25]=1

Participants

8

Reactant 5

HCID 24526Chlorine2×HCID 660593-PyrrolineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178462083HCID 178462083, compound

Product 1

HCID 178462057HCID 178462057, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from (1S)-2-trifluoromethyl-4-{N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]aminocarbonyl}benzoic acid, TBTU, diisopropylethylamine, and 3-pyrroline in tetrahydrofuran. Yield: 55%; Rf value: 0.50 (silica gel: dichloromethane/ethanol=9:1); C22H18ClF3N4O2 (462.863); mass spectrum: (M+H)+=463/465 (chlorine isotope) and (M−H)−=461/463 (chlorine isotope).

Sources & evidence

ORD record
ord-458a1cd7529242729487be661d284219
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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