1-(4-Fluoro-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline → HCID 69763736, compound

HRID 2414825Notes

Reaction equation

[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][CH:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=3)[CH2:10][CH2:9][NH:8]2)=[CH:4][CH:3]=1.[C:23]([O:27][C:28](=[O:33])[NH:29][CH2:30][CH2:31]Br)([CH3:26])([CH3:25])[CH3:24].CCN(C(C)C)C(C)C>C1COCC1>[C:23]([O:27][C:28](=[O:33])[NH:29][CH2:30][CH2:31][N:8]1[CH2:9][CH2:10][C:11]2[C:16](=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH:7]1[CH2:6][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:22][CH:21]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 1-(4-fluorobenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline (example A31, 1.05 g, 3.5 mmol) in THF (40 mL) is added (2-bromo-ethyl)-carbamic acid tert-butyl ester (example B1, 0.94 g, 4.2 mmol) and DIPEA. The reaction mixture is stirred at 70° C. in a sealed flask for 5 days. After cooling to rt, the reaction mixture is evaporated to dryness, and the residue is purified by preparative HPLC to provide the title compound.

Workup

temperatureAfter cooling to rt
customthe reaction mixture is evaporated to dryness
customthe residue is purified by preparative HPLC

Sources & evidence

ORD record: ord-cf33ce8e019049ccb201b8713b078e9f
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06815451B2

Reaction notes

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