tert-butyl N-(azetidin-3-ylmethyl)carbamate → HCID 67147599, compound

HRID 490533Notes

Reaction equation

HRID 490533 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[N:9]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:10]([C:12]3[C:20]4[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=4)[N:14]([CH3:25])[CH:13]=3)=[CH:11][C:4]=12.[C:36]([O:40][C:41](=[O:48])[NH:42][CH2:43][CH:44]1[CH2:47][NH:46][CH2:45]1)([CH3:39])([CH3:38])[CH3:37]>>[C:36]([O:40][C:41](=[O:48])[NH:42][CH2:43][CH:44]1[CH2:45][N:46]([CH2:2][C:3]2[CH:8]=[CH:7][N:6]=[C:5]3[N:9]([S:26]([C:29]4[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=4)(=[O:28])=[O:27])[C:10]([C:12]4[C:20]5[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=5)[N:14]([CH3:25])[CH:13]=4)=[CH:11][C:4]=23)[CH2:47]1)([CH3:39])([CH3:37])[CH3:38].[C:36]([O:40][C:41](=[O:48])[NH:42][CH2:43][CH:44]1[CH2:45][N:46]([CH2:2][C:3]2[CH:8]=[CH:7][N:6]=[C:5]3[NH:9][C:10]([C:12]4[C:20]5[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=5)[N:14]([CH3:25])[CH:13]=4)=[CH:11][C:4]=23)[CH2:47]1)([CH3:39])([CH3:37])[CH3:38]

Participants

4

Reactant 2

HCID 15346872tert-butyl N-(azetidin-3-ylmethyl)carbamateHCID 67147535HCID 67147535, compound

Product 2

HCID 67147599HCID 67147599, compoundYield 221.9%HCID 67147982HCID 67147982, compound

Procedure

{1-[2-(5,6-Dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]azetidin-3-ylmethyl}carbamic acid tert-butyl ester is prepared as described in Example 200b starting with 0.14 g of 4-chloromethyl-2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine and 0.123 g of azetidin-3-ylmethylcarbamic acid tert-butyl ester instead of the piperid-4-ol used in Example 200b. After purification by flash-pack chromatography (SiO2, dichloromethane/methanol 95/5 by volume as eluent), 0.154 g of {1-[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]azetidin-3-ylmethyl}carbamic acid tert-butyl ester is obtained, the characteristics of which are as follows:

Workup

  1. customAfter purification by flash-pack chromatography (SiO2, dichloromethane/methanol 95/5 by volume as eluent)

Sources & evidence

ORD record
ord-9b93a00918ad4db9abd6d6cf7f798fd1
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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