Potassium Carbonate → HCID 66891841, compound

HRID 1161991Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[C:7]2[O:11][CH:10]=[CH:9][C:8]=2[CH:12]=1)([O-:3])=[O:2].Cl[CH2:20][C:21]([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[O:22].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:24]([N:23]([CH2:26][CH3:27])[C:21](=[O:22])[CH2:20][N:16]1[CH2:15][CH2:14][N:13]([C:6]2[C:7]3[O:11][CH:10]=[CH:9][C:8]=3[CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:18][CH2:17]1)[CH3:25]

Participants

Conditions

Temperature: 225 °C

Procedure

A mixture of 1-(5-nitro-1-benzofuran-7-yl)piperazine (0.4 g, 1.6 mmol; Intermediate 21) and 2-chloro-N,N-diethylacetamide (0.48 g, 3.2 mmol) in the presence of K2CO3 (0.45 g, 3.2 mmol) in DMF was heated at 225° C. for 5 min using controlled microwave energy. The solvent was evaporated and the residue triturated with MeCN to give 0.31 g (54%) of the title compound as a yellow solid. HPLC purity 80%, RT=1.63 min (System A; 10-97% MeCN over 3 min). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.02 (t, J=7.0 Hz, 3H) 1.14 (t, J=7.0 Hz, 3H) 2.58-2.77 (m, 4H) 3.14-3.50 (m, 10H) 7.14 (d, J=2.3 Hz, 1H) 7.53 (d, J=2.3 Hz, 1H) 8.18 (dd, J=12.5, 2.3 Hz, 2H).

Workup

customThe solvent was evaporated
customthe residue triturated with MeCN

Sources & evidence

ORD record: ord-c4bcf5f32da34c728b0ebc42d9d5325c
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820675B2

Reaction notes

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