Chlorine → HCID 178474226, compound

HRID 2054033Notes

Reaction equation

HRID 2054033 reaction equation
[C:1]([N:4]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][C:11]=1[CH3:19])[CH:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2].CN(C(O[N:28]1N=[N:35][C:30]2[CH:31]=C[CH:33]=[CH:34][C:29]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C([N:45](C(C)C)CC)(C)C.ClC1C=CC2NC([C@@H](N)[CH2:60][CH2:61][S:62]C)=NC=2C=1.ClCl.Cl[CH2:70][Cl:71].[CH2:72](O)[CH3:73]>O1CCCC1>[C:1]([N:4]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([NH:45][C@@H:72]([C:73]2[NH:28][C:29]3[CH:34]=[CH:33][C:70]([Cl:71])=[CH:31][C:30]=3[N:35]=2)[CH:61]([SH:62])[CH3:60])=[O:16])=[CH:12][C:11]=1[CH3:19])[CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

8

Reactant 6

HCID 24526Chlorine2×HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 21584144Dichloromethane ethanolHCID 693097404-(N-acetyl-N-cyclopentylamino)-3-methylbenzoic acidHCID 178503691(S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulfanylpropylamine

Product 1

HCID 178474226HCID 178474226, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example 1g from 4-(N-acetyl-N-cyclopentylamino)-3-methylbenzoic acid, TBTU, diisopropylethylamine, and (1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulfanylpropylamine in tetrahydrofuran. Yield: 9%; Rf value: 0.68 (silica gel: dichloromethane/ethanol=9:1); C26H31ClN4O2S (499.076); mass spectrum: (M+H)+=499/501 (chlorine isotope) and (M−H)−=497/499 (chlorine isotope).

Sources & evidence

ORD record
ord-efe966ea45b0419fa8eb577d7fdff2c3
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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