Potassium Hydroxide → HCID 67147982, compound

HRID 490532Notes

Reaction equation

HRID 490532 reaction equation
[C:1]([O:5][C:6](=[O:47])[NH:7][CH2:8][CH:9]1[CH2:12][N:11]([CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]3[N:20]([S:37]([C:40]4[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=4)(=[O:39])=[O:38])[C:21]([C:23]4[C:31]5[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=5)[N:25]([CH3:36])[CH:24]=4)=[CH:22][C:15]=23)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>>[C:1]([O:5][C:6](=[O:47])[NH:7][CH2:8][CH:9]1[CH2:12][N:11]([CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]3[NH:20][C:21]([C:23]4[C:31]5[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=5)[N:25]([CH3:36])[CH:24]=4)=[CH:22][C:15]=23)[CH2:10]1)([CH3:3])([CH3:4])[CH3:2].[C:1]([O:5][C:6](=[O:47])[NH:7][CH2:8][CH:9]1[CH2:10][N:11]([CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[C:16]3[N:20]([S:37]([C:40]4[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=4)(=[O:39])=[O:38])[C:21]([C:23]4[C:31]5[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=5)[N:25]([CH3:36])[CH:24]=4)=[CH:22][C:15]=23)[CH2:12]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 67147982HCID 67147982, compound

Product 2

HCID 67147599HCID 67147599, compoundHCID 67147982HCID 67147982, compoundYield 49.3%

Procedure

{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 prepared as described in Example 179a starting With 0.15 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-ylmethyl}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 0.909 cm3 of 5N potassium hydroxide. After purification by flash-pack chromatography (SiO2, dichloromethane/methanol 95/5 by volume as eluent), 0.037 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-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-cbf2abf5d5e642518188e0ce4b1db1c2
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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