Diisopropylethylamine → HCID 178512776, compound

HRID 1793844Notes

Reaction equation

[C:1]1([NH:7][C:8]2[S:12][N:11]=[N:10][C:9]=2[C:13]([NH2:15])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[N:17]1([C:22](N)=[NH:23])C=CC=N1.C(N(C(C)C)CC)(C)C>N1C=CC=CC=1>[C:1]1([NH:7][C:8]2[S:12][N:11]=[N:10][C:9]=2[CH2:13][NH:15][C:22]([NH2:23])=[NH:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a 2 mL pyridine solution of 5-phenylamino-[1,2,3]thiadiazole-4-carboxylic acid amide (50 mg, 0.24 mmole), was added the powder of 1H-pyrazole-1-carboxamidine hydrochloride (235 mg, 1.59 mmole) and diisopropyl ethylamine (234 mg, 1.8 mmole). Then the mixture was heated to about 80 ° C. The reaction mixture was cooled to room temperature for 4 hours and the solvent was then evaporated. The residue was loaded onto a preparative TLC plate and eluted sequentially with neat CH2Cl2 and CH2Cl2.MeOH (4:1). A 94 mg of crude product was collected, which was further purified by another preparative TLC (silica gel, CH2Cl2.MeOH.H2O=3.6:0.4:0.06). The title compound was obtained in 40 mg (66%). 1H NMR (ppm, CDCl3): 9.33 (br. t, 1 H), 8.01 (br. s, 1 H), 7.63-7.82 (m, 2 H), 7.20-7.40 (m, 3 H), 6.37 (br. s, 2 H), 6.08 (br. s, 1 H), 4.41 (d, 2 H).

Workup

temperatureThe reaction mixture was cooled to room temperature for 4 hours
customthe solvent was then evaporated
washeluted sequentially with neat CH2Cl2 and CH2Cl2
customA 94 mg of crude product was collected
customwhich was further purified by another preparative TLC (silica gel, CH2Cl2.MeOH.H2O=3.6:0.4:0.06)

Sources & evidence

ORD record: ord-8fc5e16f7c2048f3b95aa89007d3a9e7
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022702B2

Reaction notes

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