Potassium Hydroxide → HCID 67147746, compound

HRID 490529Notes

Reaction equation

[C:1]([O:5][C:6](=[O:46])[NH:7][CH:8]1[CH2:11][N:10]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[N:19](S(C4C=CC(C)=CC=4)(=O)=O)[C:20]([C:22]4[C:30]5[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=5)[N:24]([CH3:35])[CH:23]=4)=[CH:21][C:14]=23)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>>[C:1]([O:5][C:6](=[O:46])[NH:7][CH:8]1[CH2:9][N:10]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[NH:19][C:20]([C:22]4[C:30]5[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=5)[N:24]([CH3:35])[CH:23]=4)=[CH:21][C:14]=23)[CH2:11]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 14797Potassium Hydroxide

HCID 67147714HCID 67147714, compound

Product 1

HCID 67147746HCID 67147746, compoundYield 70.7%

Procedure

{1-[2-(5,6-Dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]azetidin-3-yl}carbamic acid tert-butyl ester is prepared as described in Example 179a starting with 0.13 g of {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-yl}carbamic acid tert-butyl ester instead of the [2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl](4-trifluoromethylsulfanylbenzyl)amine used in Example 179a and 0.805 cm3 of 5N potassium hydroxide. 0.07 g of {1-[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]azetidin-3-yl}carbamic acid tert-butyl ester is obtained, the characteristics of which are as follows:

Workup

custom{1-[2-(5,6-Dimethoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl]azetidin-3-yl}carbamic acid tert-butyl ester is prepared

Sources & evidence

ORD record: ord-4d9d2d78357f47d380e9d4442fbc6b77
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528147B2

Reaction notes

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