N-bromobutanimide → HCID 14457650, compound

HRID 1195014Notes

Reaction equation

HRID 1195014 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[N:15]([C:16]([N:18]([CH3:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:17])[CH2:14][C:13]2[N:26]=[CH:27][N:28]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:12]=2[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:36]N1C(=O)CCC1=O>C(Cl)Cl>[Br:36][C:27]1[N:28]([CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:12]2[CH2:11][C@@H:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3])[N:15]([C:16]([N:18]([CH3:25])[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:17])[CH2:14][C:13]=2[N:26]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 14457646HCID 14457646, compound

Product 1

HCID 14457650HCID 14457650, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.23 g of (S)-1,4,6,7-tetrahydro-6-(t-butyldimethylsilyloxymethyl)-N-methyl-N-phenyl-1-(phenylmethyl)-5H-imidazo[4,5-c]pyridine-5-carboxamide and 10 mL of methylene chloride is stirred at room temperature and 0.45 g of N-bromosuccinimide is added. The reaction mixture is stirred for 20 min and concentrated. The residue is purified by flash chromatography on silica gel eluting with a 50% ethyl acetate-hexane mixture. The desired fractions are combined and concentrated to afford the desired product as an oil; TLC (SiO2) 50% EtOHc/hexane, Rf =0.35.

Workup

  1. stirringThe reaction mixture is stirred for 20 min
  2. concentrationconcentrated
  3. customThe residue is purified by flash chromatography on silica gel eluting with a 50% ethyl acetate-hexane mixture
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9e7e993a6d12428cbbcd5ea8d109b132
Source dataset
uspto-grants-1989_03
Patent number
US04816463

Reaction notes

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