Triethylamine → N-(5-bromo-1,3-thiazol-2-yl)adamantane-1-carboxamide

HRID 255075

Reaction equation

Br.[NH2:2][C:3]1[S:4][C:5]([Br:8])=[CH:6][N:7]=1.[C:9]12([C:19](Cl)=[O:20])[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C1COCC1.C(OCC)(=O)C>[Br:8][C:5]1[S:4][C:3]([NH:2][C:19]([C:9]23[CH2:18][CH:13]4[CH2:12][CH:11]([CH2:17][CH:15]([CH2:14]4)[CH2:16]2)[CH2:10]3)=[O:20])=[N:7][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-amino-5-bromothiazole monohydrobromide (3.00 g, 11.5 mmol), 1-adamantanecarbonyl chloride (2.74 g, 13.8 mmol), 4-dimethylaminopyridine (1.10 g, 0.90 mmol) and triethylamine (3.20 mL, 23.0 mmol) in 100 mL of THF was stirred at 80° C. for 48 hours. The mixture was cooled to ambient temperature, diluted with 100 mL of ethyl acetate and washed with brine. The layers were separated and the aqueous phase was extracted twice with 50 mL of ethyl acetate. The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated. Purification by column chromatography (SiO2, 20% ethyl acetate:80% hexane) afforded 2.55 g of the title compound: 1H NMR (400 MHz, DMSO-d6) δ 1.67-1.72 (m, 6 H) 1.92 (d, J=2.8 Hz, 6 H) 1.97-2.04 (m, 3 H) 7.55 (s, 1 H) 11.50 (br m, 1 H); MS (DCI/NH3) m/z 341 (M)+, 343 (M+2)+.

Workup

temperatureThe mixture was cooled to ambient temperature
washwashed with brine
customThe layers were separated
extractionthe aqueous phase was extracted twice with 50 mL of ethyl acetate
dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customPurification by column chromatography (SiO2, 20% ethyl acetate:80% hexane)

Sources & evidence

ORD record: ord-2906da847d944d67938b9b2a5c2bd97b
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875639B2

Linked notes

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