Diisopropylethylamine → HCID 67539952, compound

HRID 1192351Notes

Reaction equation

HRID 1192351 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[N:17][C:18](Cl)=[C:13]3[C:12]([Br:20])=[N:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].CCN(C(C)C)C(C)C>CC(O)C>[C:24]([O:23][C:21]([N:28]1[CH2:33][CH2:32][N:31]([C:18]2[N:17]=[CH:16][N:15]=[C:14]3[N:10]([S:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)(=[O:9])=[O:8])[N:11]=[C:12]([Br:20])[C:13]=23)[CH2:30][CH2:29]1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 86053731HCID 86053731, compound

Product 1

HCID 67539952HCID 67539952, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of 1-Benzenesulfonyl-3-bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (1.8 g, 4.8 mmol), Boc-piperazine (1.4 g, 7.2 mmol) and DIPEA (2.1 mL, 12 mmol) in IPA (40 mL) was stirred and heated at reflux overnight. The reaction mixture was cooled to −10° C., the solids isolated by vacuum filtration, rinsed with cold IPA and dried further on high vacuum line to give 4-(1-Benzenesulfonyl-3-bromo-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (1.7 g, 67%) as a white powder. LCMS (APCI+) m/z 523 and 525 [M+H]+; Rt: 3.57 min. 1H NMR (CDCl3, 400 MHz) δ 8.53 (1H, s), 8.23 (2H, d, J 8.5 Hz), 7.65 (1H, t, J 6.9 Hz), 7.54 (2H, t, J 7.8 Hz), 3.82-3.79 (4H, m), 3.60-3.57 (4H, m), 1.48 (9H, s.)

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customthe solids isolated by vacuum filtration
  4. washrinsed with cold IPA
  5. customdried further on high vacuum line

Sources & evidence

ORD record
ord-8f8de2101d1642b59811661a54474117
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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