1H-Indazol-6-amine → 7-(2-Chloroethoxy)-4-(1H-indazol-6-ylamino)-6-methoxyquinoline-3-carbonitrile

HRID 1595811Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](Cl)=[C:10]([C:15]#[N:16])[CH:11]=[N:12]2)=[CH:7][C:6]=1[O:18][CH3:19].[NH2:20][C:21]1[CH:29]=[C:28]2[C:24]([CH:25]=[N:26][NH:27]2)=[CH:23][CH:22]=1.Cl.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>CC(C)=O.CCCCCC.COCCO>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:20][C:21]3[CH:29]=[C:28]4[C:24]([CH:25]=[N:26][NH:27]4)=[CH:23][CH:22]=3)=[C:10]([C:15]#[N:16])[CH:11]=[N:12]2)=[CH:7][C:6]=1[O:18][CH3:19]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 0.50 g (1 equivalent) of 7-(2-chloro-ethoxy)-4-chloro-6-methoxy-quinoline-3-carbonitrile, 0.25 g (1.1 equivalents) of 6-aminoindazole, 0.22 g (1.1 equivalents) of pyridine hydrochloride and 15 ml of 2-methoxyethanol was heated in 120° C. oil bath for 2 hours. The reaction progress was monitored by thin layer chromatography (acetone/hexane 1:1). After 2 hours, the reaction mixture was cooled to room temperature; a total of 25 ml of 1M sodium bicarbonate was added and the reaction was stirred for 1 hour. The resultant precipitate was collected, washed with water and dried in vacuo at 60° C. overnight to give 0.645 g (97%) of the desired product. :mass spectrum (electrospray m/e): M+H=393.9 (M+H)+; Analysis calculated for C20H16ClN5O2: 2 H2O: Calculated C:55.88; H:4.69; N:16.29; Found C:55.63; H:4.78; N:15.24

Workup

temperaturethe reaction mixture was cooled to room temperature
customThe resultant precipitate was collected
washwashed with water
customdried in vacuo at 60° C. overnight

Sources & evidence

ORD record: ord-55f9320a4e5f4d13b4aa677325ad93be
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288082B1

Reaction notes

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