Chlorine → HCID 178503696, compound

HRID 2053846Notes

Reaction equation

HRID 2053846 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12])[C:5]([OH:7])=O.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:49][C:50]1[CH:64]=[CH:63][C:53]2[NH:54][C:55]([C@@H:57]([NH2:62])[CH2:58][CH2:59][S:60][CH3:61])=[N:56][C:52]=2[CH:51]=1.ClCl>O1CCCC1.ClCCl.CO>[Cl:49][C:50]1[CH:64]=[CH:63][C:53]2[NH:54][C:55]([C@@H:57]([NH:62][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][C:10]([C:11]([N:13]4[CH2:17][CH2:16][CH2:15][CH2:14]4)=[O:12])=[C:2]([CH3:1])[CH:3]=3)[CH2:58][CH2:59][S:60][CH3:61])=[N:56][C:52]=2[CH:51]=1

Participants

8

Reactant 5

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 120686863-Methyl 4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 178503691(S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulfanylpropylamine

Product 1

HCID 178503696HCID 178503696, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulfanylpropylamine in tetrahydrofuran. Yield: 64%; Rf value: 0.5 (silica gel; dichloromethane/methanol=9:1); C24H27ClN4O2S (471.02); mass spectrum: (M+H)+=471/473 (chlorine isotope).

Sources & evidence

ORD record
ord-d0815422caac47d488f9abd0a6c085d1
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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