Acetic Anhydride → HCID 178474774, compound

HRID 2053877Notes

Reaction equation

HRID 2053877 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C@H:5]([NH:16][C:17](=[O:32])[C:18]1[CH:23]=[CH:22][C:21]([C:24]([N:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)=[O:25])=[C:20]([CH3:31])[CH:19]=1)[C:6]1[NH:10][C:9]2[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:8]=2[N:7]=1.[C:33](OC(=O)C)(=[O:35])[CH3:34].C(N(CC)CC)C.ClCl>O1CCCC1.ClCCl.CO>[C:33]([NH:1][CH2:2][CH2:3][CH2:4][C@H:5]([NH:16][C:17](=[O:32])[C:18]1[CH:23]=[CH:22][C:21]([C:24]([N:26]2[CH2:27][CH2:28][CH2:29][CH2:30]2)=[O:25])=[C:20]([CH3:31])[CH:19]=1)[C:6]1[NH:10][C:9]2[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:8]=2[N:7]=1)(=[O:35])[CH3:34]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 24526Chlorine2×HCID 178427168HCID 178427168, compound

Product 1

HCID 178474774HCID 178474774, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 124 from (1S)—N-[4-amino-1-(5-chloro-1H-benzimidazol-2-yl)butyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide, acetic anhydride, and triethylamine in tetrahydrofuran. Yield: 73%; Rf value: 0.73 (silica gel; dichloromethane/methanol=95:5); C26H30ClN5O3 (496.01); mass spectrum: (M+H)+=496/498 (chlorine isotope) and (M−H)-=494/496 (chlorine isotope).

Sources & evidence

ORD record
ord-50efca5f3fb349bc8c2069078d8c73cf
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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