HCID 86620965, compound → HCID 24947589, compound

HRID 1667402Notes

Reaction equation

HRID 1667402 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([N:22]([CH3:24])[CH3:23])=[N:17][N:16]=[C:15]3I)=[O:11])[CH:6]=[CH:7][CH:8]=1.[C:28]([Cu])#[N:29]>N1C=CC=CC=1>[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[C:18]([N:22]([CH3:24])[CH3:23])=[N:17][N:16]=[C:15]3[C:28]#[N:29])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 86620965HCID 86620965, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 24947589HCID 24947589, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 1-dimethylamino-4-iodo-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (40 mg, 0.082 mmol), pyridine (3 mL) and CuCN (22 mg, 0.247 mmol) was heated to 85° C. for 2 h and concentrated. Column chromatography (Hexanes/EtOAc) afforded the desired compound (14 mg, 44.2%) as a yellow solid. 1H-NMR (CDCl3) δ: 3.45 (s, 6H), 7.40-7.44 (m, 1H), 7.49 (t, 1H), 8.01 (d, 1H), 8.12 (s, 1H), 8.23 (d, 1H), 8.31 (s, 1H), 8.38 (d, 1H), 9.13 (s, 1H). m/z (M+1) 386.20.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-d9a6cbe0781243058c1a07184dd5c033
Source dataset
uspto-grants-2011_10
Patent number
US08044041B2

Reaction notes

Loading…