HCID 24947400, compound → HCID 24947224, compound

HRID 1803486Notes

Reaction equation

[F:1][C:2]([F:32])([F:31])[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]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:17][N:16]=[C:15]3I)=[O:11])[CH:6]=[CH:7][CH:8]=1.[C:33]([Cu])#[N:34]>N1C=CC=CC=1>[F:1][C:2]([F:32])([F:31])[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]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:17][N:16]=[C:15]3[C:33]#[N:34])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 1-benzylamino-4-iodo-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (62 mg, 0.11 mmol) in pyridine was added CuCN (30 mg, 0.34 mmol). The solution was heated to 90° C. for 1 hour, then concentrated under vacuum. Flash chromatography (hexanes/EtOAc) was used to obtain 4-Cyano-1-benzylamino-phthalazine-6-carboxylic acid (3-trifluoromethyl-phenyl)-amide (25 mg, 50%) as a yellow solid. 1H-NMR (DMSO-d6) δ: 4.94 (d, 2H), 7.26 (m, 1H), 7.34 (t, 2H), 7.43 (d, 2H), 7.52 (d, 1H), 7.66 (t, 1H), 8.10 (d, 1H), 8.26 (s, 1H), 8.52 (m, 2H), 8.65 (d, 1H), 9.21 (t, 1H), 11.0 (s, 1H).

Workup

concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-998a9a7a54b947058b990b1d29ae4f8c
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349836B2

Reaction notes

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