Isobutylene oxide → 6-Hydroxy-2-{4-[(S)-7-(2-hydroxy-2-methyl-propyl)-2,7-diaza-spiro[4.4]non-2-yl]-phenyl}-3,4-dihydro-2H-isoquinolin-1-one

HRID 69435

Reaction equation

[CH2:1]1[C@@:5]2([CH2:9][CH2:8][NH:7][CH2:6]2)[CH2:4][CH2:3][N:2]1[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([OH:26])[CH:22]=3)[C:17]2=[O:27])=[CH:12][CH:11]=1.[CH3:28][C:29]1([O:32][CH2:31]1)[CH3:30].[Br-].[Li+].CN1C(=O)CCC1>O.C(OCC)(=O)C>[OH:26][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[C:17](=[O:27])[N:16]([C:13]1[CH:14]=[CH:15][C:10]([N:2]3[CH2:3][CH2:4][C@:5]4([CH2:9][CH2:8][N:7]([CH2:28][C:29]([OH:32])([CH3:31])[CH3:30])[CH2:6]4)[CH2:1]3)=[CH:11][CH:12]=1)[CH2:25][CH2:24]2

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 2-[(S)-4-(2,7-diaza-spiro[4.4]non-2-yl)-phenyl]-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one (0.50 g), isobutylene oxide (0.10 g), lithium bromide (0.12 g) and NMP (1 mL) was heated at 65° C. for 5 hours. The cooled reaction mixture was distributed between ethyl acetate and water. The organic phase was dried over magnesium sulfate and concentrated. In this way the product was obtained with molecular weight 435.57 (C26H33N3O3); MS (ESI): 436 (M+H+).

Workup

customThe cooled reaction mixture
dry with materialThe organic phase was dried over magnesium sulfate
concentrationconcentrated
customIn this way the product was obtained with molecular weight 435.57 (C26H33N3O3)

Sources & evidence

ORD record: ord-6387aed4dbab48d0a1e4b19c018ce08e
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822495B2

Linked notes

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