Methanol → HCID 178427160, compound

HRID 2053844Notes

Reaction equation

HRID 2053844 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([NH:27][C:28](=[O:43])[C:29]1[CH:34]=[CH:33][C:32]([C:35]([N:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)=[O:36])=[C:31]([CH3:42])[CH:30]=1)[C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:19]=2[N:18]=1)=O)C1C=CC=CC=1.I[Si](C)(C)C.CO>ClCCl>[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([NH:27][C:28](=[O:43])[C:29]1[CH:34]=[CH:33][C:32]([C:35]([N:37]2[CH2:38][CH2:39][CH2:40][CH2:41]2)=[O:36])=[C:31]([CH3:42])[CH:30]=1)[C:17]1[NH:21][C:20]2[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:19]=2[N:18]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 178427167HCID 178427167, compound

Product 1

HCID 178427160HCID 178427160, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.3 g (0.49 mmol) of N-[(1S)-5-(benzyloxycarbonylamino)-1-(5-chloro-1H-benzimidazol-2-yl)pentyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide is dissolved in 15 mL of dichloromethane and, after the addition of 0.25 mL (0.76 mmol) of iodotrimethylsilane, stirred for 3 hours at ambient temperature. Then 10 mL of methanol is added and the mixture is stirred for a further 30 minutes. The solvent is distilled off and the residue is chromatographed on silica gel, eluting with dichloromethane/methanol (80:20). Yield: 0.22 g (96%); Rf value: 0.15 (silica gel; dichloromethane/methanol=9:1); C25H30ClN5O2 (468.00); mass spectrum: (M+H)+=468/470 (chlorine isotope).

Workup

  1. stirringthe mixture is stirred for a further 30 minutes
  2. distillationThe solvent is distilled off
  3. customthe residue is chromatographed on silica gel
  4. washeluting with dichloromethane/methanol (80:20)

Sources & evidence

ORD record
ord-2af1974caebd4cf9b8b1bce3d78961b1
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

Loading…