Triethylamine → HCID 66705835, compound

HRID 2276389Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][N:36]=[C:37]=[O:38])=[CH:31][CH:30]=1>CN(C=O)C.O>[F:28][C:29]1[CH:30]=[CH:31][C:32]([CH2:35][NH:36][C:37](=[O:38])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([C@@H:8]3[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]3)=[CH:4][CH:3]=2)=[CH:33][CH:34]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of (S)-tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate (100 mg) in DMF (3.5 ml) were added sequentially triethylamine (62 μl) and 1-fluoro-4-(isocyanatomethyl)benzene (58.4 μl) and the mixture was stirred at 60° C. for 17 h. The suspension was cooled to room temperature, then diluted with water and extracted twice with EtOAc. The combined organic phases were washed sequentially with water and saturated brine. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was purified was purified by flash chromatography (silica gel; gradient: EtOAc/heptane) to afford (S)-tert-butyl 2-(4-(3-(4-fluorobenzyl)ureido)phenyl)morpholine-4-carboxylate (164 mg, quant.) as a white solid. MS (ISP): 374.0 ([M+H—C4H8]+).

Workup

temperatureThe suspension was cooled to room temperature
extractionextracted twice with EtOAc
washThe combined organic phases were washed sequentially with water and saturated brine
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified
customwas purified by flash chromatography (silica gel; gradient: EtOAc/heptane)

Sources & evidence

ORD record: ord-dac00ade86254573aed4a49a8688c353
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09132136B2

Reaction notes

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