Diisopropylethylamine → HCID 178512776, compound

HRID 1182211Notes

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, 1H), 8.01 (br. s, 1H), 7.63-7.82 (m, 2H), 7.20-7.40 (m, 3H), 6.37 (br. s, 2H), 6.08 (br. s, 1H), 4.41 (d, 2H).

Workup

temperatureThe reaction mixture was cooled to room temperature for 4 hours
customthe solvent was then evaporated
washeluted sequentially with neat CH2Cl2 and CH2Cl2:MeOH (4:1)
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-f9f2f4fe750b4a3386181035d4686d85
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288556B2

Reaction notes

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