Triethylamine → HCID 67313820, compound

HRID 1011451Notes

Reaction equation

C(N(CC)CC)C.[CH:8]1([NH:11][CH2:12][C:13]2[CH:14]=[C:15]([C:21]3[CH:22]=[CH:23][C:24]4[O:28][N:27]=[C:26]([NH:29][CH2:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:25]=4[CH:35]=3)[CH:16]=[CH:17][C:18]=2[O:19][CH3:20])[CH2:10][CH2:9]1.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C(Cl)Cl>[CH:8]1([N:11]([CH2:12][C:13]2[CH:14]=[C:15]([C:21]3[CH:22]=[CH:23][C:24]4[O:28][N:27]=[C:26]([NH:29][CH2:30][C:31]([CH3:32])([CH3:34])[CH3:33])[C:25]=4[CH:35]=3)[CH:16]=[CH:17][C:18]=2[O:19][CH3:20])[S:37]([CH3:36])(=[O:39])=[O:38])[CH2:9][CH2:10]1

Participants

Conditions

Temperature: -70 °C

Procedure

Triethylamine (0.14 mL, 0.99 mmol, 1.5 equiv.) was added to a solution of 5-(3-((cyclopropylamino)methyl)-4-methoxyphenyl)-N-neopentylbenzo[d]isoxazol-3-amine (exemplary compound 45) (0.25 g, 0.66 mmol, 1 equiv.) in DCM (10 mL) and the mixture was subsequently cooled to −70° C. Methanesulphonic acid chloride (0.06 mL, 0.79 mmol, 1.2 equiv.) was added in drops and the mixture was heated slowly to RT and stirred for 15 hours. The reaction mixture was diluted with DCM (50 mL) and extracted with sat. aq. sodium hydrogen carbonate sol. (1×10 mL) and sat. aq. NaCl solution (1×10 mL), dried (MgSO4) and the solvent removed in a vacuum. After column-chromatographic purification (EtOAc/DCM; 1:1), the desired product (0.21 g, >99%) is obtained.

Workup

temperaturethe mixture was heated slowly to RT
extractionextracted with sat. aq. sodium hydrogen carbonate sol. (1×10 mL) and sat. aq. NaCl solution (1×10 mL)
dry with materialdried (MgSO4)
customthe solvent removed in a vacuum
customAfter column-chromatographic purification (EtOAc/DCM; 1:1)

Sources & evidence

ORD record: ord-fe9b71d2d6594623a754f6a4854fb019
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977360B2

Reaction notes

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