Triethylamine → HCID 178462075, compound

HRID 2053909Notes

Reaction equation

HRID 2053909 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([C:10]1[CH:30]=[CH:29][C:13]([C:14]([NH:16][C@H:17]([C:19]2[NH:23][C:22]3[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:21]=3[N:20]=2)[CH3:18])=[O:15])=[CH:12][C:11]=1[Cl:31])=[O:9].[CH3:32][S:33](Cl)(=[O:35])=[O:34].C(N(CC)CC)C.ClCl>O1CCCC1.ClCCl.C(O)C>[Cl:31][C:11]1[CH:12]=[C:13]([CH:29]=[CH:30][C:10]=1[C:8]([N:4]1[CH2:5][CH2:6][CH2:7][C@@H:3]1[CH2:2][NH:1][S:33]([CH3:32])(=[O:35])=[O:34])=[O:9])[C:14]([NH:16][C@H:17]([C:19]1[NH:23][C:22]2[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:21]=2[N:20]=1)[CH3:18])=[O:15]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24526Chlorine2×HCID 31297Methanesulfonyl chlorideHCID 178462071HCID 178462071, compound

Product 1

HCID 178462075HCID 178462075, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 125 from 4-((2R)-2-aminomethylpyrrolidin-1-ylcarbonyl)-3-chloro-N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)ethyl]benzamide, methanesulfonic acid chloride, and triethylamine in tetrahydrofuran. Yield: 62%; Rf value: 0.31 (silica gel; dichloromethane/ethanol=9:1); C23H25Cl2N5O4S (538.45); mass spectrum: (M+H)+=538/549/542 (chlorine isotope) and (M−H)−=536/538/540 (chlorine isotope).

Sources & evidence

ORD record
ord-36062a04fbbf4791a0ddbd99d2ccb154
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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