Cyanogen Bromide → HCID 59432365, compound

HRID 507094Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:21]2[C:13](=[CH:14][C:15]3[CH2:16][O:17][CH2:18][C:19]=3[CH:20]=2)[C@@H:12]([NH:22][CH2:23][C:24]2[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:38]([N:41](C(C)C)CC)(C)C.N#CBr>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:21]2[C:13](=[CH:14][C:15]3[CH2:16][O:17][CH2:18][C:19]=3[CH:20]=2)[C@@H:12]([N:22]([CH2:23][C:24]2[CH:25]=[C:26]([C:34]([F:36])([F:37])[F:35])[CH:27]=[C:28]([C:30]([F:32])([F:31])[F:33])[CH:29]=2)[C:38]#[N:41])[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of (S)-9-(3,5-bis-trifluoromethyl-benzylamino)-1,3,6,7,8,9-hexahydro-2-oxa-5-aza-cyclohepta[f]indene-5-carboxylic acid tert-butyl ester (1.75 mmol) in tetrahydrofuran (7 mL) and diisopropyl ethylamine (5.25 mmol), add cyanogenbromide (5.25 mmol) and heat to 65° C. After stirring overnight, cool to room temperature and dilute with ethyl acetate (10 mL). Wash the organic portion with water (10 mL), followed by brine (10 mL). Dry the organic portion over sodium sulfate, filter, and remove solvent under vacuum. Chromatograph the product over silica gel, eluting with ethyl acetate/hexane (5-35%) to afford the title compound as an oil. MS (ES+): 554.2 (M−H).

Workup

temperaturecool to room temperature
washWash the organic portion with water (10 mL)
dry with materialDry the organic portion over sodium sulfate
filtrationfilter
customremove solvent under vacuum
washChromatograph the product over silica gel, eluting with ethyl acetate/hexane (5-35%)

Sources & evidence

ORD record: ord-093be78995c54fedad2fc4e67e59d62f
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786108B2

Reaction notes

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