Diisopropylethylamine → HCID 66668105, compound

HRID 2176429Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]2[S:11][C:10]([CH2:12][CH3:13])=[N:9][N:5]2[C:6](=[O:8])[CH:7]=1.[N:14]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(N(CC)C(C)C)(C)C>C(#N)C>[CH2:12]([C:10]1[S:11][C:4]2=[N:3][C:2]([N:17]3[CH2:16][CH2:15][N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18]3)=[CH:7][C:6](=[O:8])[N:5]2[N:9]=1)[CH3:13]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 7-chloro-2-ethyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one (2.0 g, 9.27 mmol, 1.0 equiv) in 50 mL of anhydrous acetonitrile in a microwave vial is added tert-butyl 1-piperazinecarboxylate (2.073 g, 11.13 mmol, 1.2 equiv) followed by N,N-diisopropylethylamine (4.86 mL, 27.8 mmol, 3.0 equiv). The mixture is heated in a microwave reactor for 25 min at 150° C. Upon completion, the mixture is concentrated in vacuo to give crude tert-butyl 4-(2-ethyl-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate as a yellow oil. This material is advanced directly to the next step.

Workup

concentrationUpon completion, the mixture is concentrated in vacuo

Sources & evidence

ORD record: ord-e0cc6342acc44ec190ea8b4ecef6cdd0
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09066948B2

Reaction notes

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