Ethylenediamine → HCID 60054736, compound

HRID 1792870

Reaction equation

HRID 1792870 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:27][CH2:26][CH2:25][C:9]32[N:13]([CH3:14])[C:12](=[O:15])[N:11]([C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)[C:10]3=[O:24])=[CH:4][CH:3]=1.[C:28]([Cu])#[N:29].C(N)CN>CN1C(=O)CCC1>[Cl:23][C:18]1[CH:17]=[C:16]([N:11]2[C:10](=[O:24])[C@:9]3([CH2:25][CH2:26][CH2:27][C@H:8]3[C:5]3[CH:6]=[CH:7][C:2]([C:28]#[N:29])=[CH:3][CH:4]=3)[N:13]([CH3:14])[C:12]2=[O:15])[CH:21]=[C:20]([Cl:22])[CH:19]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 220252906-(4-Bromophenyl)-3-(3,5-dichlorophenyl)-1-methyl-1,3-diazaspiro[4.4]nonane-2,4-dioneHCID 178418546HCID 178418546, compound

Product 1

HCID 60054736HCID 60054736, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 6-(4-bromophenyl)-3-(3,5-dichlorophenyl)-1-methyl-1,3-diazaspiro[4.4]nonane-2,4-dione (1 g, 2.1 mmol) (Example 1) and CuCN (0.45 g, 5 mmol) in NMP was heated to 180° C. for 6 h. After cooling, the reaction mixture was poured on a mixture of ice and ethylene diamine and extracted twice with DCM. The brown residue was chromatographed over silica gel to yield 4-[(5R*,6S*)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3-diazaspiro[4.4] non-6-yl]benzonitrile as a beige solid. 1H NMR (CDCl3): 7.62 (2H, d, J=8.1 Hz), 7.25–7.3 (3H, m), 6.67 (2H, br s), 3.45 (1H, dd, J1=12.8 Hz, J2=6.4 Hz), 3.16 (3H, s), 2.4–2.7 (1H, m), 1.8–2.4 (5H, m).

Workup

  1. temperatureAfter cooling
  2. extractionextracted twice with DCM
  3. customThe brown residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-de085f3f17b64cf198ba4cd20b06db1d
Source dataset
uspto-grants-2006_07
Patent number
US07078420B2

Linked notes

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