N-bromobutanimide → HCID 66738157, compound

HRID 2047020Notes

Reaction equation

HRID 2047020 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]([CH:13]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[C:23]([N:25]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[N:22]3[N:42]=[CH:43][C:44]([C:45]4[CH:46]=[N:47][C:48]5[C:53]([CH:54]=4)=[CH:52][CH:51]=[CH:50][CH:49]=5)=[C:21]3[N:20]=2)[CH2:15][CH2:14]1)=[O:12]>C(#N)C>[CH3:9][O:10][C:11]([CH:13]1[CH2:14][CH2:15][CH:16]([C:19]2[C:24]([Br:1])=[C:23]([N:25]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:31])([CH3:32])[CH3:33])[N:22]3[N:42]=[CH:43][C:44]([C:45]4[CH:46]=[N:47][C:48]5[C:53]([CH:54]=4)=[CH:52][CH:51]=[CH:50][CH:49]=5)=[C:21]3[N:20]=2)[CH2:17][CH2:18]1)=[O:12]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 674941714-{7-[Bis-(2-trimethylsilanyl-ethoxymethyl)-amino]-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-5-yl}-cyclohexanecarboxylic acid methyl ester

Product 1

HCID 66738157HCID 66738157, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-bromosuccinimide (148 mg, 0.832 mmol) was added to a solution of 4-{7-[bis-(2-trimethylsilanyl-ethoxymethyl)-amino]-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-5-yl}-cyclohexanecarboxylic acid methyl ester (500 mg, 0.756 mmol) in acetonitrile (10 mL). The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo and the resulting oil is then purified via silica gel chromatography (0% to 30% ethyl acetate in hexanes gradient) to yield the title compound (530 mg, 95% yield) as yellow oil. LC-MS: 740 [M+H].

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting oil is then purified via silica gel chromatography (0% to 30% ethyl acetate in hexanes gradient)

Sources & evidence

ORD record
ord-48cec505b3f947aca2c114cbde642ca7
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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