HCID 68462964, compound → HCID 68463013, compound

HRID 506210Notes

Reaction equation

[Cl:1][C:2]1[C:7]([NH2:8])=[CH:6][N:5]=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12.F[C:13]1[C:18]([C:19]#[N:20])=[CH:17][N:16]=[CH:15][C:14]=1[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28]COC)=[C:23]([O:32][CH3:33])[CH:22]=1>CS(C)=O>[Cl:1][C:2]1[C:7]([NH:8][C:13]2[C:18]([C:19]#[N:20])=[CH:17][N:16]=[CH:15][C:14]=2[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:32][CH3:33])[CH:22]=2)=[CH:6][N:5]=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-chloro-1H-pyrrolo[2,3-b]pyridin-5-amine (see e.g., Tetrahedron Lett., 45(11), 2317-2319 (2004)) (0.30 mmol, 51 mg) and 4-fluoro-5-[3-methoxy-4-(2-methoxyethoxy)phenyl]nicotinonitrile (0.23 mmol, 60 mg) in 2 mL DMSO was heated to 100° C. overnight. The product was purified by a preparative HPLC followed by silica gel chromatography (CH2Cl2/MeOH) to give 4-[(4-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)amino]-5-(3,4-dimethoxyphenyl)nicotinonitrile (23 mg). HPLC retention time: 7.9 min.(g) and MS: 406.2 (M+H) and HRMS: 406.10747.

Workup

customThe product was purified by a preparative HPLC

Sources & evidence

ORD record: ord-1c2c541b07674a73b67bdc1b49cfa918
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781591B2

Reaction notes

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