Diisopropylethylamine → HCID 11514839, compound

HRID 2217331Notes

Reaction equation

I.[S:2]1[C:6]2[CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:5]=2[N:4]=[C:3]1[NH2:14].Cl.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=1.C(N(C(C)C)CC)(C)C>ClC(Cl)C>[S:2]1[C:6]2[CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:5]=2[N:4]=[C:3]1[NH:14][C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A suspension of 8H-Indeno[1,2-d]thiazol-2-ylamine hydroiodide 1a (Prepared in Example 1, Step 1, mg; mmol), nicotinoyl chloride hydrochloride (92 mg; 0.50 mmol) and diisopropylethylamine (0.50 mL; 2.77 mmol) in dichloroethane was heated in a sealed tube to 120° C. in a microwave oven for 10 minutes. The mixture was allowed to cool to room temperature and the solvent removed in vacuo. The residue was taken up into 2 M sodium carbonate solution and extracted with ethyl acetate. The extracts were dried (sodium sulfate), filtered and concentrated in vacuo. The crude product was chromatographed on silica gel (eluent=50% ethyl acetate/hexanes to 100% ethyl acetate/hexanes gradient) to provide 43 mg of N-(8H-Indeno[1,2-d]thiazol-2-yl)-nicotinamide 7. EI-HRMS m/e calcd for C16H11N4OS (M+) 293.0623, found 293.0620.

Workup

temperatureto cool to room temperature
customthe solvent removed in vacuo
extractionextracted with ethyl acetate
dry with materialThe extracts were dried (sodium sulfate)
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was chromatographed on silica gel (eluent=50% ethyl acetate/hexanes to 100% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record: ord-2974063c7a2f4a8c90b33e077f51e383
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07407977B2

Reaction notes

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