Methanol → (1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-(1H-tetrazol-5-yl)propylamine

HRID 551213Notes

Reaction equation

HRID 551213 reaction equation
C(OC([NH:11][C@H:12]([C:20]1[NH:24][C:23]2[CH:25]=[CH:26][C:27]([Cl:29])=[CH:28][C:22]=2[N:21]=1)[CH2:13][CH2:14][C:15]1[NH:19][N:18]=[N:17][N:16]=1)=O)C1C=CC=CC=1.I[Si](C)(C)C.CO>ClCCl>[Cl:29][C:27]1[CH:26]=[CH:25][C:23]2[NH:24][C:20]([C@@H:12]([NH2:11])[CH2:13][CH2:14][C:15]3[NH:19][N:18]=[N:17][N:16]=3)=[N:21][C:22]=2[CH:28]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 178523880HCID 178523880, compound

Product 1

HCID 178511819(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-(1H-tetrazol-5-yl)propylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.10 g (4.45 mmol) (1S)—N-(benzyloxycarbonyl)-1-(5-chloro-1H-benzimidazol-2-yl)-3-(1H-tetrazol-5-yl)-propylamine in 30 ml dichloromethane are combined with 1.9 ml (13.4 mmol) iodo-trimethylsilane and stirred for 16 hours at ambient temperature. Then 20 ml of methanol are added, the mixture is stirred for a further 30 minutes at ambient temperature and the reaction mixture is evaporated down completely i. vac. The residue is purified by chromatography on silica gel (eluting gradient: dichloromethane/(ethanol/conc. ammonia 95:5)=70/30→60:40).

Workup

  1. stirringthe mixture is stirred for a further 30 minutes at ambient temperature
  2. customthe reaction mixture is evaporated down completely
  3. customThe residue is purified by chromatography on silica gel (eluting gradient: dichloromethane/(ethanol/conc. ammonia 95:5)=70/30→60:40)

Sources & evidence

ORD record
ord-541a1651f3a04a95b5ea73aac27b7577
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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