N-bromobutanimide → HCID 67494233, compound

HRID 2047145Notes

Reaction equation

HRID 2047145 reaction equation
[CH3:1][Si:2]([CH3:52])([CH3:51])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:43][O:44][CH2:45][CH2:46][Si:47]([CH3:50])([CH3:49])[CH3:48])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH:29]2[CH2:34][CH2:33][N:32]([C:35]3[O:39][C:38]([C@H:40]([OH:42])[CH3:41])=[N:37][N:36]=3)[CH2:31][CH2:30]2)[CH:9]=1.C1C(=O)N([Br:60])C(=O)C1>C(#N)C>[CH3:48][Si:47]([CH3:50])([CH3:49])[CH2:46][CH2:45][O:44][CH2:43][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:51])([CH3:1])[CH3:52])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH:29]2[CH2:30][CH2:31][N:32]([C:35]3[O:39][C:38]([C@H:40]([OH:42])[CH3:41])=[N:37][N:36]=3)[CH2:33][CH2:34]2)[C:9]=1[Br:60]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 66733702HCID 66733702, compound

Product 1

HCID 67494233HCID 67494233, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (R)-1-(5-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidin-1-yl)-1,3,4-oxadiazol-2-yl)ethanol (32 mg, 0.04 mmol) in acetonitrile (1 mL) was added NBS (7 mg, 0.04 mmol) and the resulting solution was stirred for 10 minutes and concentrated. The residue was purified on silica gel. Elution with EtOAc provided a relatively pure product (9 mg).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified on silica gel
  3. washElution with EtOAc

Sources & evidence

ORD record
ord-5f151ef5e08548eaad8d2fc46b8f9015
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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