Methylamine → HCID 69056193, compound

HRID 2100583Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:20][C@H:19]2[C@@H:10]([N:11]([CH2:26][C:27]([OH:29])=O)[C:12](=[O:25])[C:13]3[C:14]([C:21]([F:24])([F:23])[F:22])=[CH:15][CH:16]=[CH:17][C:18]=32)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:30]([N:32](CC)CC)C.ClC(OCC)=O.CN>C1COCC1>[CH3:30][NH:32][C:27](=[O:29])[CH2:26][N:11]1[C@H:10]2[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:20][C@@H:19]2[C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([C:21]([F:24])([F:22])[F:23])[C:13]=2[C:12]1=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-((3aR,9bS)-2-(tert-butoxycarbonyl)-5-oxo-6-(trifluoromethyl)-1,2,3,3a-tetrahydro-5H-pyrrolo[3,4-c]isoquinolin-4(9bH)-yl)acetic acid (40 mg, 0.1 mmol) in 4 mL of THF at 0° C. was added triethylamine (0.017 mL, 0.12 mmol) and ethyl chloroformate (0.012 mL, 0.12 mmol). The reaction was allowed to stir for 30 min at 0° C. and then there was added methylamine (0.1 mL of a 2.0M solution in THF, 0.2 mmol). The resulting mixture was stirred for 1 h at 0° C. and then was quenched with 10 mL of 1N HCl. The mixture was extracted with ethyl acetate and the organics were washed with sat'd aq NaHCO3 and brine, dried (MgSO4), filtered through a pad of silica gel and concentrated in vacuo to afford 30 mg (70%) of the title compound which was sufficiently pure to be used without purification. LRMS (ESI): 428.24 (M+H)+.

Workup

stirringThe resulting mixture was stirred for 1 h at 0° C.
customwas quenched with 10 mL of 1N HCl
extractionThe mixture was extracted with ethyl acetate
washthe organics were washed with sat'd aq NaHCO3 and brine
dry with materialdried (MgSO4)
filtrationfiltered through a pad of silica gel
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1937bf7797c44e80a4ba6979e86a59ba
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572805B2

Reaction notes

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