Chlorine → HCID 178427202, compound

HRID 2053867Notes

Reaction equation

HRID 2053867 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(O[N:26]1N=[N:33][C:28]2[CH:29]=[CH:30]C=[CH:32][C:27]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH:40]([N:43](C(C)C)CC)([CH3:42])[CH3:41].Cl[CH2:50][Cl:51].C[OH:53].N.ClCl>O1CCCC1>[Cl:51][C:50]1[CH:30]=[CH:29][C:28]2[NH:33][C:41]([C@@H:40]([NH:43][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)[CH2:42][OH:53])=[N:26][C:27]=2[CH:32]=1

Participants

7

Reactant 5

HCID 24526Chlorine2×HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 120686863-Methyl 4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 21584172Ammonia methanol dichloromethane

Product 1

HCID 178427202HCID 178427202, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and (R)-(5-chloro-1H-benzimidazol-2-yl)-2-hydroxyethylamine in tetrahydrofuran. Yield: 43%; Rf value: 0.28 (silica gel; dichloromethane/methanol/ammonia=9:1:0.1); C22H23ClN4O3 (426.90); mass spectrum: (M+H)+=427/429 (chlorine isotope) and (M−H)−=425/427 (chlorine isotope).

Sources & evidence

ORD record
ord-08ddd225241e4af78fb1a85712df5e11
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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