Chlorine → HCID 178462055, compound

HRID 2054025Notes

Reaction equation

HRID 2054025 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[C:23]([N:25]1[CH2:29][CH2:28][CH2:27][CH:26]1[CH2:30][CH2:31][C:32]([OH:34])=O)=[O:24])[C:5]([NH:7][C@H:8]([C:10]1[NH:14][C:13]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:12]=2[N:11]=1)[CH3:9])=[O:6].CN(C(O[N:43]1N=NC2C=[CH:47][CH:48]=[CH:49][C:44]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.N1CCCC1.ClCl>O1CCCC1.ClCCl.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[C:23]([N:25]1[CH2:29][CH2:28][CH2:27][CH:26]1[CH2:30][CH2:31][C:32]([N:43]1[CH2:44][CH2:49][CH2:48][CH2:47]1)=[O:34])=[O:24])[C:5]([NH:7][C@H:8]([C:10]1[NH:14][C:13]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:12]=2[N:11]=1)[CH3:9])=[O:6]

Participants

8

Reactant 5

HCID 24526ChlorineHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178462056HCID 178462056, compound

Product 1

HCID 178462055HCID 178462055, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from 3-chloro-N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)ethyl]-4-[(2R/S)-2-(hydroxycarbonylethyl)pyrrolidin-1-ylcarbonyl]benzamide, TBTU, diisopropylethylamine, and pyrrolidine in tetrahydrofuran. Yield: 22%; Rf value: 0.53 (silica gel: dichloromethane/ethanol=9:1); C28H31Cl2N5O3 (556.497); mass spectrum: (M+H)+=556/558/560 (chlorine isotope).

Sources & evidence

ORD record
ord-b748af0de792459d928dbd9cf556b094
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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