Water → HCID 67516958, compound

HRID 2173459Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([CH2:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]3[CH:33]=[CH:32][C:27]4[C:28](=[O:31])[O:29][CH2:30][C:26]=4[CH:25]=3)[CH2:18][CH2:17]2)=[O:15])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[N:11][N:10]=[N:9]1.[C:34]([Cu])#[N:35].O>CN(C=O)C>[O:15]=[C:14]([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]2[CH:33]=[CH:32][C:27]3[C:28](=[O:31])[O:29][CH2:30][C:26]=3[CH:25]=2)[CH2:18][CH2:17]1)[CH2:13][C:4]1[CH:5]=[CH:6][C:7]([N:8]2[CH:12]=[N:11][N:10]=[N:9]2)=[C:2]([CH:3]=1)[C:34]#[N:35]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 5-[2-(4-{[3-iodo-4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)ethyl]-2-benzofuran-1(3H)-one (190 mg, 034 mmol) and CuCN (47 mg, 0.52 mmol) in 2 ml of anhydrous DMF was heated to 110° C. under N2 for 30 min. The reaction was cooled to ambient temperature, and then 15 ml of water was added. Extracted with DCM and the organic layer was dried over anhydrous sodium sulfate and concentrated. The crude product was purified via prep-TLC to afford 5-(2-oxo-2-{4-[2-(1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazin-1-yl}ethyl)-2-(1H-tetrazol-1-yl)benzonitrile. 1H-NMR (400 MHz, CD3CN) δ ppm 9.36 (s, 1H), 7.85 (s, 1H), 7.72˜7.79 (m, 3H), 7.44˜7.50 (m, 2H), 5.30 (s, 2H), 3.87 (s, 2H), 2.49 (t, J=7.5 Hz, 21H), 2.64 (t, J=7.2 Hz, 2H), 2.65˜2.70 (m, 2H), 2.46˜2.53 (m, 4H).

Workup

temperatureThe reaction was cooled to ambient temperature
extractionExtracted with DCM
dry with materialthe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated
customThe crude product was purified via prep-TLC

Sources & evidence

ORD record: ord-c10fc3c5ab574a8cb9221190ce690c10
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056859B2

Reaction notes

Loading…