2-Bromoethanol → HCID 71534974, compound

HRID 2175142Notes

Reaction equation

HRID 2175142 reaction equation
[N:1]1([C:8]2[CH:9]=[N:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([S:18][C:19]2[N:23]4[CH:24]=[C:25]([C:28]5[CH:29]=[N:30][N:31]([CH3:33])[CH:32]=5)[CH:26]=[CH:27][C:22]4=[N:21][N:20]=2)=[CH:13][CH:12]=3)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:35][CH2:36][OH:37].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:33][N:31]1[CH:32]=[C:28]([C:25]2[CH:26]=[CH:27][C:22]3[N:23]([C:19]([S:18][C:14]4[CH:15]=[C:16]5[C:11](=[CH:12][CH:13]=4)[N:10]=[CH:9][C:8]([N:1]4[CH2:7][CH2:6][CH2:5][N:4]([CH2:35][CH2:36][OH:37])[CH2:3][CH2:2]4)=[CH:17]5)=[N:20][N:21]=3)[CH:24]=2)[CH:29]=[N:30]1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 71534669HCID 71534669, compound

Product 1

HCID 71534974HCID 71534974, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(1,4-Diazepan-1-yl)-6-(6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-ylthio)quinoline (Example 19—see in Table below) (15 mg, 0.033 mmol), 2-bromoethanol (12.33 mg, 0.099 mmol) and K2CO3 (9.08 mg, 0.066 mmol) in DMF (0.5 ml) was stirred at rt for 24 hr. The mixture was purified by prep-HPLC to give the title compound (6 mg, yield 36%). [Method 1D]

Workup

  1. customThe mixture was purified by prep-HPLC

Sources & evidence

ORD record
ord-bd76297cc68b4250afa78c33da29afd7
Source dataset
uspto-grants-2015_06
Patent number
US09062045B2

Reaction notes

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