Diisopropylethylamine → HCID 66999920, compound

HRID 906906Notes

Reaction equation

C([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[F:20])[CH:10]([CH:21]([O:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][N:25]=2)[CH3:22])[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O.CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][CH:21]([CH:10]2[CH:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[F:20])[CH2:12][NH:8][CH2:9]2)[CH3:22])=[N:25][CH:26]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-{(RS)-1-[(3SR,4RS)-1-benzyl-4-(2,4-difluoro-phenyl)-pyrrolidin-3-yl]-ethoxy}-5-chloro-pyridine 570 mg (1.32 mmol) dissolved in toluene (12 mL) were added 0.43 mL (3.96 mmol) of 1-chloroethyl chloroformate and 0.68 mL (3.96 mmol) of Hunig's base. The reaction mixture was heated at 100° C. for one hour. After cooling down to RT, volatiles were removed under vacuo and the crude was dissolved in MeOH (10 mL). The reaction mixture was heated at 85° C. for 30 minutes and after cooling down to RT, volatiles were removed under vacuo and the residue was directly purified on column chromatography (SiO2, CH2Cl2/MeOH 9:1) yielded 350 mg (78%) of the title compound as a light yellow oil. ES-MS m/e: 339.1 (M+H+).

Workup

temperatureAfter cooling down to RT
customvolatiles were removed under vacuo
dissolutionthe crude was dissolved in MeOH (10 mL)
temperatureThe reaction mixture was heated at 85° C. for 30 minutes
temperatureafter cooling down to RT
customvolatiles were removed under vacuo
customthe residue was directly purified on column chromatography (SiO2, CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record: ord-2228fbb832e84705909adb5e140e7e92
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012998B2

Reaction notes

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