Chlorine → HCID 178426914, compound

HRID 2053856Notes

Reaction equation

HRID 2053856 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:62]=[CH:61][C:53]2[NH:54][C:55]([C:57]3([NH2:60])[CH2:59][CH2:58]3)=[N:56][C:52]=2[CH:51]=1.ClCl>O1CCCC1.C(OCC)(=O)C.C(O)C>[Cl:49][C:50]1[CH:62]=[CH:61][C:53]2[NH:54][C:55]([C:57]3([NH:60][C:5](=[O:7])[C:4]4[CH:8]=[CH:9][C:10]([C:11]([N:13]5[CH2:17][CH2:16][CH2:15][CH2:14]5)=[O:12])=[C:2]([CH3:1])[CH:3]=4)[CH2:58][CH2:59]3)=[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 178507167HCID 178507167, compound

Product 1

HCID 178426914HCID 178426914, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584252Ethanol ethylacetateSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and 1-(5-chloro-1H-benzimidazol-2-yl)cyclopropylamine in tetrahydrofuran. Yield: 44%; Rf value: 0.37 (silica gel; ethyl acetate/ethanol=9:1); C23H23ClN4O2 (422.91); mass spectrum: (M+H)+=423/425 (chlorine isotope).

Sources & evidence

ORD record
ord-d7e654a3f25a40f1a1ea06761c179166
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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