Isopropanol → Azd 7009

HRID 1376020Notes

Reaction equation

C(O)(C)C.[C:5]([O:9][C:10](=[O:23])[NH:11][CH2:12][CH2:13][N:14]1[CH2:21][CH:20]2[O:22][CH:16]([CH2:17][NH:18][CH2:19]2)[CH2:15]1)([CH3:8])([CH3:7])[CH3:6].[O:24]1[CH2:26][C@H:25]1[CH2:27][O:28][C:29]1[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=1>O>[C:33]([C:32]1[CH:35]=[CH:36][C:29]([O:28][CH2:27][C@@H:25]([OH:24])[CH2:26][N:18]2[CH2:17][CH:16]3[O:22][CH:20]([CH2:21][N:14]([CH2:13][CH2:12][NH:11][C:10](=[O:23])[O:9][C:5]([CH3:8])([CH3:6])[CH3:7])[CH2:15]3)[CH2:19]2)=[CH:30][CH:31]=1)#[N:34]

Participants

Conditions

Temperature: 66 °C

Procedure

iso-Propanol (5 mL) and water (0.5 mL) were added to [2-(9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl)ethyl]carbamic acid tert-butyl ester (see Example 3 (Alternative I) above; 0.43 g, 1.6 mmol) and 0.4-[(2S)-oxiranylmethoxy]benzonitrile(0.280 g, 1.6 mmol; see Preparation D above) was added. The mixture was heated at 66° C. for 19 hours (reaction was complete in 2 hours). The solvent was evaporated to dryness under reduced pressure to give the title compound as an off-white solid (0.71 g, 100%).

Workup

custom(reaction was complete in 2 hours)
customThe solvent was evaporated to dryness under reduced pressure

Sources & evidence

ORD record: ord-c47d8baf84a64c95991e893c0b702486
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07169921B2

Reaction notes

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