Chlorine → HCID 178474789, compound

HRID 2054047Notes

Reaction equation

HRID 2054047 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]([NH:13][C@H:14]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:18]=3[N:17]=2)[CH3:15])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[C:57]([N:60]([CH2:62][C@H:63]1[CH2:67][CH2:66][CH2:65][NH:64]1)[CH3:61])(=[O:59])[CH3:58].ClCl>O1CCCC1.ClCCl.C(O)C>[C:57]([N:60]([CH2:62][C@H:63]1[CH2:67][CH2:66][CH2:65][N:64]1[C:4]([C:3]1[CH:7]=[CH:8][C:9]([C:11]([NH:13][C@H:14]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:18]=3[N:17]=2)[CH3:15])=[O:12])=[CH:10][C:2]=1[Cl:1])=[O:5])[CH3:61])(=[O:59])[CH3:58]

Participants

8

Reactant 5

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 45088475(R)-2-[(N-acetyl-N-methylamino)methyl]pyrrolidineHCID 178462084(1S)-2-chloro-4-{N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]aminocarbonyl}benzoic acid

Product 1

HCID 178474789HCID 178474789, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from (1S)-2-chloro-4-{N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]aminocarbonyl}benzoic acid, TBTU, diisopropylethylamine, and (R)-2-[(N-acetyl-N-methylamino)methyl]pyrrolidine in tetrahydrofuran. Yield: 17%; Rf value: 0.40 (silica gel: dichloromethane/ethanol=9:1); C25H27Cl2N5O3 (516.426); mass spectrum: (M+H)+=516/518/520 (chlorine isotope).

Sources & evidence

ORD record
ord-8f96926145aa48ac9aa909ead9636420
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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