4-Aminobenzonitrile → HCID 58636775, compound

HRID 1158992Notes

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:9]([CH3:20])=[N:10][C:11]([CH:17]2[CH2:19][CH2:18]2)=[C:12]([CH:16]=1)[C:13](O)=[O:14])#[N:2].[NH2:24][C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=1>>[C:1]([C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][CH:23]=1)[CH2:6][O:7][C:8]1[C:9]([CH3:20])=[N:10][C:11]([CH:17]2[CH2:19][CH2:18]2)=[C:12]([CH:16]=1)[C:13]([NH:24][C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=1)=[O:14])#[N:2]

Participants

Reactant 2

HCID 133964-Aminobenzonitrile

HCID 58636727HCID 58636727, compound

Product 1

HCID 58636775HCID 58636775, compoundYield 33.2%

Procedure

The amide coupling of 5-(3-cyano-benzyloxy)-2-cyclopropyl-6-methyl-nicotinic acid (185) (230 mg, 0.7 mmol) and 4-amino-benzonitrile (106 mg, 0.9 mmol), as described in Example 67, gave 5-(3-cyano-benzyloxy)-N-(4-cyano-phenyl)-2-cyclopropyl-6-methyl-nicotinamide (186) (95 mg, 27% yield).

Sources & evidence

ORD record: ord-29fd6e9a41bd4341ac50ffd5e6438c20
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812037B2

Reaction notes

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