Benzoyl chloride → HCID 178427102, compound

HRID 2053854Notes

Reaction equation

HRID 2053854 reaction equation
[NH2:1][CH2:2][CH:3]([NH:14][C:15](=[O:30])[C:16]1[CH:21]=[CH:20][C:19]([C:22]([N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:23])=[C:18]([CH3:29])[CH:17]=1)[C:4]1[NH:8][C:7]2[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:6]=2[N:5]=1.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(N(CC)CC)C.ClCl>O1CCCC1.ClCCl.CO>[C:31]([NH:1][CH2:2][CH:3]([NH:14][C:15](=[O:30])[C:16]1[CH:21]=[CH:20][C:19]([C:22]([N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:23])=[C:18]([CH3:29])[CH:17]=1)[C:4]1[NH:8][C:7]2[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:6]=2[N:5]=1)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 24526Chlorine2×HCID 178427101HCID 178427101, compound

Product 1

HCID 178427102HCID 178427102, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 125 from N-[2-amino-1-(5-chloro-1H-benzimidazol-2-yl)ethyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide, benzoyl chloride, and triethylamine in tetrahydrofuran. Yield: 65%; Rf value: 0.32 (silica gel; dichloromethane/methanol=19:1); C29H28ClN5O3 (530.03); mass spectrum: (M+H)+=530/532 (chlorine isotope) and (M−H)-=528/530 (chlorine isotope).

Sources & evidence

ORD record
ord-425bb6ea2ce14a3b946cb5276b548d6c
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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