3-Cyano-5-(pentafluoro-lambda6-sulphanyl)benzoic acid → 3-Cyano-N-(3-{6-[1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-1H-imidazo[1,2-b]pyrazol-1-yl}-4-methylphenyl)-5-(pentafluoro-lambda6-sulphanyl)benzamide

HRID 1055688Notes

Reaction equation

HRID 1055688 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:14]=[C:15]4[N:20]([C:21]5[CH:22]=[C:23]([CH:25]=[CH:26][C:27]=5[CH3:28])[NH2:24])[CH:19]=[CH:18][N:16]4[N:17]=3)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[C:31]([C:33]1[CH:34]=[C:35]([CH:39]=[C:40]([S:42]([F:47])([F:46])([F:45])([F:44])[F:43])[CH:41]=1)[C:36](O)=[O:37])#[N:32]>>[C:31]([C:33]1[CH:34]=[C:35]([CH:39]=[C:40]([S:42]([F:46])([F:47])([F:43])([F:44])[F:45])[CH:41]=1)[C:36]([NH:24][C:23]1[CH:25]=[CH:26][C:27]([CH3:28])=[C:21]([N:20]2[C:15]3[N:16]([N:17]=[C:13]([C:11]4[CH:10]=[N:9][N:8]([CH2:7][C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:30][CH:29]=5)[CH:12]=4)[CH:14]=3)[CH:18]=[CH:19]2)[CH:22]=1)=[O:37])#[N:32]

Participants

3

Reactant 2

HCID 896998123-Cyano-5-(pentafluoro-lambda6-sulphanyl)benzoic acidHCID 897000273-{6-[1-(4-Methoxybenzyl)-1H-pyrazol-4-yl]-1H-imidazo[1,2-b]pyrazol-1-yl}-4-methylaniline

Product 1

HCID 896995663-Cyano-N-(3-{6-[1-(4-methoxybenzyl)-1H-pyrazol-4-yl]-1H-imidazo[1,2-b]pyrazol-1-yl}-4-methylphenyl)-5-(pentafluoro-lambda6-sulphanyl)benzamide

Procedure

80 mg (0.16 mmol) of the compound of Example 60A and 66 mg (0.24 mmol) of the compound of Example 23A were reacted with one another analogously to Example 48A. In deviation from the work-up described therein, here, the mixture was separated directly into its components by preparative HPLC (Method 21). The product-containing fractions were concentrated under reduced pressure and the residue was dried under high vacuum. This gave 84 mg (64% of theory, 80% pure) of the title compound.

Workup

  1. customhere, the mixture was separated directly into its components by preparative HPLC (Method 21)
  2. concentrationThe product-containing fractions were concentrated under reduced pressure
  3. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-62509c420c4342d18528512d93d1e75c
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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