HCID 67191587, compound → HCID 67190977, compound

HRID 2355508Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C@:8]([C@@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([NH:24][C@H:25]([CH2:33][N:34]([CH3:44])[C:35]([O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])=[O:36])[CH2:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:23])[CH2:17]2)([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=[CH:6][CH:7]=1.[C:45]([Cu])#[N:46]>CN(C=O)C>[C:45]([C:2]1[CH:3]=[C:4]([C@:8]([C@@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([NH:24][C@H:25]([CH2:33][N:34]([CH3:44])[C:35]([O:37][CH2:38][CH2:39][Si:40]([CH3:41])([CH3:42])[CH3:43])=[O:36])[CH2:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:23])[CH2:17]2)([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=[CH:6][CH:7]=1)#[N:46]

Participants

Conditions

Temperature: 220 °C

Procedure

To a stirred mixture of (3R)-3-((S)-1-(3-bromophenyl)-1-hydroxy-5-methoxypentyl)-N—((S)-1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-yl)piperidine-1-carboxamide (40.0 mg, 0.06 mmol) in DMF (0.5 mL), was added CuCN (excess), and the resulting solution was heated in a CEM microwave reactor at 220° C. for 20 min. The mixture was cooled to rt, and purified by preparative HPLC to give (3R)-3-((S)-1-(3-Cyanophenyl)-1-hydroxy-5-methoxypentyl)-N—((S)-1-cyclohexyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)-amino)propan-2-yl)piperidine-1-carboxamide (8.0 mg, 22%). MS m/z 665 (M+Na+).

Workup

temperatureThe mixture was cooled to rt
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-326625ccbcc8467e8b90c3568e1d570e
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754737B2

Reaction notes

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