3-Cyano-5-(trifluoromethoxy)benzoic acid → 3-Cyano-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(trifluoromethoxy)benzamide
Reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N:9]1[C:16]2[N:12]([N:13]=[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:15]=2)[CH:11]=[CH:10]1.[C:23]([C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([O:34][C:35]([F:38])([F:37])[F:36])[CH:33]=1)[C:28](O)=[O:29])#[N:24]>>[C:23]([C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([O:34][C:35]([F:36])([F:38])[F:37])[CH:33]=1)[C:28]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([CH3:1])=[C:3]([N:9]2[C:16]3[N:12]([N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[CH:11]=[CH:10]2)[CH:4]=1)=[O:29])#[N:24]Participants
3
Procedure
Analogously to the procedure for Example 33, 50 mg (0.17 mmol) of the compound of Example 6A and 40 mg (0.18 mmol) of the compound of Example 41A were reacted with one another. After purification of the crude product by preparative HPLC, the product-containing fractions were concentrated to a small residual volume and made alkaline with a little saturated aqueous sodium bicarbonate solution. The precipitate formed was filtered off, washed with water and dried. This gave 56 mg (65% of theory) of the title compound.
Workup
- customAfter purification of the crude product by preparative HPLC
- concentrationthe product-containing fractions were concentrated to a small residual volume
- customThe precipitate formed
- filtrationwas filtered off
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-a39771ff0898428aa8d860ccf33c282c
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394309B2
Reaction notes
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