HCID 86620964, compound → HCID 24947590, compound

HRID 1803487Notes

Reaction equation

HRID 1803487 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](I)=[N:17][N:16]=[C:15]3[N:23]([CH3:25])[CH3:24])=[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]([C:28]#[N:29])=[N:17][N:16]=[C:15]3[N:23]([CH3:25])[CH3:24])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 86620964HCID 86620964, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 24947590HCID 24947590, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-dimethylamino-1-iodo-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (85 mg, 0.175 mmol), pyridine (3 mL) and CuCN (46 mg, 0.514 mmol) was heated to 85° C. for 2 h and concentrated. Column chromatography (Hexanes/EtOAc) afforded the desired compound (38 mg, 56.7%) as a yellow solid. 1H-NMR (CDCl3) δ: 3.44 (s, 6H), 7.30-7.34 (m, 1H), 7.42 (t, 1H), 8.00-8.04 (m, 2H), 8.07 (d, 1H), 8.66 (dd, 1H), 8.78 (s, 1H), 10.26 (bs, 1H). m/z (M+1) 386.20.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-80d78c670a0d4000ac585b6372e9e39b
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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