N-bromobutanimide → Tert-butyl 4-(7-amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate

HRID 2047185Notes

Reaction equation

HRID 2047185 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8](COCC[Si](C)(C)C)COCC[Si](C)(C)C)[N:5]2[N:25]=[CH:26][C:27]([C:28]3[CH:29]=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:4]2[N:3]=1.C(N(CC)C(C)C)(C)C.[C:47]([N:54]1[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]1)([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48].[Br:60]N1C(=O)CCC1=O>C(#N)C.CN1C(=O)CCC1>[NH2:8][C:6]1[N:5]2[N:25]=[CH:26][C:27]([C:28]3[CH:29]=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:4]2[N:3]=[C:2]([N:57]2[CH2:56][CH2:55][N:54]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:59][CH2:58]2)[C:7]=1[Br:60]

Participants

7

Reactant 4

HCID 67184N-bromobutanimideHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86664780(5-Chloro-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-7-yl)-bis-(2-trimethylsilanyl-ethoxymethyl)-amine

Product 1

HCID 66738195Tert-butyl 4-(7-amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

To a 20 mL scintillation vial was charged 5-chloro-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)-ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (0.09 mmol, 50 mg), NMP (1 mL), N,N-diisopropylethylamine (0.36 mmol, 63 μL), and 4-N-Boc-piperazine (0.27 mmol, 50 mg). The resulting solution was heated to 200° C. in microwave synthesizer for 30 minutes. Upon completion, the NMP was removed in vacuo as an azeotrope using chlorobenzene. This residue was dissolved in acetonitrile (1 mL) to which N-bromosuccinimide (0.10 mmol, 17.7 mg) was added. This reaction mixture was allowed to stir at room temperature for 2 hours. The reaction mixture was concentrated in vacuo and tert-butyl 4-(7-amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate used without further purification.

Workup

  1. customUpon completion, the NMP was removed in vacuo as an azeotrope
  2. additionwas added
  3. concentrationThe reaction mixture was concentrated in vacuo and tert-butyl 4-(7-amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate
  4. customused without further purification

Sources & evidence

ORD record
ord-6392e0cc995c45bf809a4b9aa1414717
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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