2-Bromopropane → 3-[4-(N-(1-carbomethoxy-1-phenylmethyl)-N-iso-propylamino)phenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]-pyridine

HRID 1492617Notes

Reaction equation

HRID 1492617 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)([CH3:45])[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]([CH3:45])[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 63582-BromopropaneHCID 10251994HCID 10251994, compoundHCID 178418261HCID 178418261, compound

Product 1

HCID 189506003-[4-(N-(1-carbomethoxy-1-phenylmethyl)-N-iso-propylamino)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 isopropyl 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-886a5c00a2314ce8891230ea2df62939
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

Loading…