3-Aminobenzonitrile → HCID 58636869, compound

HRID 1158995Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[CH2:6][O:7][C:8]1[C:16]([CH3:17])=[N:15][C:14]([CH:18]2[CH2:20][CH2:19]2)=[CH:13][C:9]=1[C:10]([OH:12])=O)#[N:2].[NH2:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[C:28]#[N:29]>>[C:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[CH2:6][O:7][C:8]1[C:16]([CH3:17])=[N:15][C:14]([CH:18]2[CH2:20][CH2:19]2)=[CH:13][C:9]=1[C:10]([NH:24][C:25]1[CH:32]=[CH:31][CH:30]=[C:27]([C:28]#[N:29])[CH:26]=1)=[O:12])#[N:2]

Participants

Reactant 2

HCID 167023-Aminobenzonitrile

HCID 58636735HCID 58636735, compound

Product 1

HCID 58636869HCID 58636869, compoundYield 24.1%

Procedure

The amide coupling of 3-(3-cyano-benzyloxy)-6-cyclopropyl-2-methyl-isonicotinic acid (189) (128 mg, 0.4 mmol) and 3-aminobenzonitrile (59 mg, 0.4 mol), as described in Example 67, gave 3-(3-cyano-benzyloxy)-N-(3-cyano-phenyl)-6-cyclopropyl-2-methyl-isonicotinamide (192) (39.4 mg, 23% yield).

Sources & evidence

ORD record: ord-5abacc457fee480eb9b95711185b0f22
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812037B2

Reaction notes

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