Chlorine → HCID 178427186, compound

HRID 2053896Notes

Reaction equation

HRID 2053896 reaction equation
C(OC([NH:11][CH2:12][CH2:13][C@H:14]([NH:25][C:26](=[O:41])[C:27]1[CH:32]=[CH:31][C:30]([C:33]([N:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)=[O:34])=[C:29]([CH3:40])[CH:28]=1)[C:15]1[NH:19][C:18]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:17]=2[N:16]=1)=O)C1C=CC=CC=1.I[Si](C)(C)C.ClCCl.C(O)C.ClCl>ClCCl>[NH2:11][CH2:12][CH2:13][C@H:14]([NH:25][C:26](=[O:41])[C:27]1[CH:32]=[CH:31][C:30]([C:33]([N:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)=[O:34])=[C:29]([CH3:40])[CH:28]=1)[C:15]1[NH:19][C:18]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:17]=2[N:16]=1

Participants

6

Reactant 4

HCID 24526ChlorineHCID 85247Trimethylsilyl iodideHCID 21584144Dichloromethane ethanolHCID 178427189N-[(1S)-3-(benzyloxycarbonylamino)-1-(5-chloro-1H-benzimidazol-2-yl)propyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide

Product 1

HCID 178427186HCID 178427186, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared analogously to Example 94 from N-[(1S)-3-(benzyloxycarbonylamino)-1-(5-chloro-1H-benzimidazol-2-yl)propyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide and iodotrimethylsilane in dichloromethane. Yield: quantitative; Rf value: 0.25 (silica gel; dichloromethane/ethanol=4:1); C23H26ClN5O2 (439.94); mass spectrum: (M+H)+=440/442 (chlorine isotope).

Sources & evidence

ORD record
ord-2e8f3cde28064d1580ff69e63896acc2
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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