2-Bromobutane → 3-[4-(N-(1-carbomethoxy-1-phenylmethyl)-N-sec-butylamino)phenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]-pyridine

HRID 1492616Notes

Reaction equation

HRID 1492616 reaction equation
[Li]N([Si](C)(C)C)[Si](C)(C)C.[C:11]([CH:15]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][N:30]2[C:34]3=[N:35][C:36]([CH3:40])=[CH:37][C:38]([CH3:39])=[C:33]3[N:32]=[C:31]2[CH2:41][CH3:42])=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([O:13][CH3:14])=[O:12].[CH:43](Br)([CH2:45][CH3:46])[CH3:44]>>[C:11]([CH:15]([N:22]([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][N:30]2[C:34]3=[N:35][C:36]([CH3:40])=[CH:37][C:38]([CH3:39])=[C:33]3[N:32]=[C:31]2[CH2:41][CH3:42])=[CH:25][CH:24]=1)[CH:43]([CH2:45][CH3:46])[CH3:44])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([O:13][CH3:14])=[O:12]

Participants

4

Reactant 3

HCID 65542-BromobutaneHCID 10251994HCID 10251994, compoundHCID 178418261HCID 178418261, compound

Product 1

HCID 104580453-[4-(N-(1-carbomethoxy-1-phenylmethyl)-N-sec-butylamino)phenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]-pyridine

Procedure

Using the general procedure for the alkylation of secondary amines with LiN(TMS)2 described in Step A of Example 29, 3-[4-(N-(1-carbomethoxy -1-phenylmethyl)amino)phenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]-pyridine (Step A, Example 28) was alkylated with sec-butyl bromide. Standard workup and purification by flash chromatography afforded the title compound.

Workup

  1. customStandard workup and purification by flash chromatography

Sources & evidence

ORD record
ord-92e693bd85ce4fb49038156d222c48c9
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

Loading…