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

HRID 1492615Notes

Reaction equation

HRID 1492615 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]1([CH2:46]Br)[CH2:45][CH2:44]1>>[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)[CH2:46][CH:43]1[CH2:45][CH2:44]1)[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 81503BromomethylcyclopropaneHCID 10251994HCID 10251994, compoundHCID 178418261HCID 178418261, compound

Product 1

HCID 104129943-[4-(N-(1-carbomethoxy-1-phenylmethyl)-N-cyclopropylmethylamino)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 cyclopropylmethyl 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-80e117ef98e9454589ef4079f7796040
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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