Chlorine → HCID 178462059, compound

HRID 2054009Notes

Reaction equation

HRID 2054009 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]([OH:6])=O.CN(C(ON1N=[N:41][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40]C1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH:48]([N:51](C(C)C)[CH2:52]C)(C)C.CN(CC1CCCN1)C.ClCl>O1CCCC1.CO>[Cl:1][C:2]1[CH:10]=[C:9]([CH:8]=[CH:7][C:3]=1[C:4]([N:41]1[CH2:36][CH2:37][CH2:38][C:39]1([CH3:40])[N:51]([CH3:52])[CH3:48])=[O:6])[C:11]([NH:13][C@H:14]([C:16]1[NH:20][C:19]2[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:18]=2[N:17]=1)[CH3:15])=[O:12]

Participants

8

Reactant 5

HCID 24526Chlorine2×HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 12658081N,N-dimethyl-1-(pyrrolidin-2-yl)methanamineHCID 178462084(1S)-2-chloro-4-{N-[1-(5-chloro-1H-benzimidazol-2-yl)ethyl]aminocarbonyl}benzoic acid

Product 1

HCID 178462059HCID 178462059, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

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 rac-2-(dimethylaminomethyl)pyrrolidine in tetrahydrofuran. Yield: 50%; Rf value: 0.32 (Reversed phase RP 8: methanol/5% sodium chloride solution=6:4); C24H27Cl2N5O2 (488.416); mass spectrum: (M+H)+=488/490/492 (chlorine isotope) and (M−H)−=486/488/490 (chlorine isotope).

Sources & evidence

ORD record
ord-131f705be09e48768738204722ea7ea7
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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