N-BOC-ethylenediamine → Ethyl 2-[2-(tert-butoxycarbonylamino)ethylamino]-5-methylamino-thiazole-4-carboxylate

HRID 631826Notes

Reaction equation

Br[C:2]1[S:3][C:4]([NH:12][CH3:13])=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[NH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].CCOP(O)N(C(C)C)C(C)C>O1CCOCC1>[C:20]([O:19][C:18]([NH:17][CH2:16][CH2:15][NH:14][C:2]1[S:3][C:4]([NH:12][CH3:13])=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1)=[O:24])([CH3:23])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 2-bromo-5-methylamino-thiazole-4-carboxylate (546 mg, 2.059 mmol) and tert-butyl N-(2-aminoethyl)carbamate (1.3 g, 8.11 mmol) were combined in anhydrous 1,4-dioxane (15 ml). EDIPA (3 ml, 17.2 mmol) was added and the mixture was heated in a sealed tube for 23 hours at 100° C. The mixture was cooled to room temperature and partitioned between DCM and a saturated solution of sodium bicarbonate. Layers were separated, the aqueous phase was extracted twice with DCM and the combined organic layers were dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography (silica, gradient of 30 to 100% ethyl acetate in heptane) to yield 185 mg (0.537 mmol, 26%) MS(ESI) m/z=345.2 [M+1]+.

Workup

temperatureThe mixture was cooled to room temperature
custompartitioned between DCM
customLayers were separated
extractionthe aqueous phase was extracted twice with DCM
dry with materialthe combined organic layers were dried over sodium sulfate
customThe solvent was removed under reduced pressure
customthe residue was purified by column chromatography (silica, gradient of 30 to 100% ethyl acetate in heptane)
customto yield 185 mg (0.537 mmol, 26%) MS(ESI) m/z=345.2 [M+1]+

Sources & evidence

ORD record: ord-6c7966313d6e483986bb44f2c77ff9be
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321724B2

Reaction notes

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