Diisopropylethylamine → HCID 66668749, compound

HRID 2176436Notes

Reaction equation

HRID 2176436 reaction equation
Cl[C:2]1[N:3]=[C:4]2[S:11][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=3)=[N:9][N:5]2[C:6](=[O:8])[CH:7]=1.[N:21]1([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.CCN(C(C)C)C(C)C>CC#N>[N+:18]([C:14]1[CH:13]=[C:12]([C:10]2[S:11][C:4]3=[N:3][C:2]([N:24]4[CH2:23][CH2:22][N:21]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:26][CH2:25]4)=[CH:7][C:6](=[O:8])[N:5]3[N:9]=2)[CH:17]=[CH:16][CH:15]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 66668846HCID 66668846, compound

Product 1

HCID 66668749HCID 66668749, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

To 7-chloro-2-(3-nitrophenyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one (1.0 g, 3.24 mmol) in MeCN (30 ml) in a microwave vial is added tert-butyl 1-piperazinecarboxylate (0.724 g, 3.89 mmol) followed by DIPEA (1.697 ml, 9.72 mmol). The mixture is heated in the microwave to 150° C. for 25 min., cooled and concentrated in vacuo and purified via column chromatography on a 50 g snap column with 0-10% MeOH/DCM gradient elution to give tert-butyl 4-(2-(3-nitrophenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (1.44 g, 3.14 mmol, 97% yield) as a tan solid.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. custompurified via column chromatography on a 50 g snap column with 0-10% MeOH/DCM gradient elution

Sources & evidence

ORD record
ord-5bb17b2674fd4941b5b0b97d64e72538
Source dataset
uspto-grants-2015_06
Patent number
US09066948B2

Reaction notes

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