Isopropylamine → 6-{[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazole-3-carbonyl]-amino}-5-cyano-1H-indazole-7-carboxylic acid isopropylamide
Reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]3[O:22][C:21](=[O:23])[C:20]4[C:15](=[C:16](C#C)[CH:17]=[C:18]5[CH:26]=[N:25][NH:24][C:19]5=4)[N:14]=3)=[CH:11][C:10]([C:29]([F:32])([F:31])[F:30])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH:33]([NH2:36])([CH3:35])[CH3:34].[C:37](#[N:39])C.O>>[CH:33]([NH:36][C:21]([C:20]1[C:15]([NH:14][C:13]([C:12]2[N:8]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[N:9]=[C:10]([C:29]([F:32])([F:31])[F:30])[CH:11]=2)=[O:22])=[C:16]([C:37]#[N:39])[CH:17]=[C:18]2[C:19]=1[NH:24][N:25]=[CH:26]2)=[O:23])([CH3:35])[CH3:34]Participants
4
Reactant 3
Product 1
Procedure
To a mixture of 426 mg of the above 7-[2-(3-chloro-pyridin-2-yl)-5-trifluoromethyl-2H-pyrazol-3-yl]-5-ethynyl-1H-8-oxa-1,2,6-triaza-cyclopenta[a]naphthalen-9-one in 7 mL of 4:1 (v/v) mixture of acetonitrile/water is added 0.79 mL (9.3 mmol) of isopropylamine. The reaction mixture is stirred during 4 hours at ambient temperature and then concentrated in vacuo. After purification by flash chromatography (SiO2, hexane/ethyl acetate 4:1), 250 mg (38%) of product are obtained as a yellow solid; LC/MS:516/518 (M+H)+; m.p.: 226-229° C.
Workup
- concentrationconcentrated in vacuo
- customAfter purification by flash chromatography (SiO2, hexane/ethyl acetate 4:1), 250 mg (38%) of product
- customare obtained as a yellow solid
Sources & evidence
- ORD record
- ord-5ec3e922dec04b07b61a3f5af059692d
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658801B2
Reaction notes
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