Diisopropylethylamine → 3-Cyano-N-{2-hydroxy-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-lambda6-sulphanyl)benzamide

HRID 1055746Notes

Reaction equation

HRID 1055746 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[C:15]3[N:11]([N:12]=[C:13]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)[CH:14]=3)[CH:10]=[CH:9]2)[C:3]=1[OH:22].[C:23]([C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([S:34]([F:39])([F:38])([F:37])([F:36])[F:35])[CH:33]=1)[C:28](O)=[O:29])#[N:24].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[C:23]([C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([S:34]([F:38])([F:39])([F:35])([F:36])[F:37])[CH:33]=1)[C:28]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[C:15]3[N:11]([N:12]=[C:13]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)[CH:14]=3)[CH:10]=[CH:9]2)[C:3]=1[OH:22])=[O:29])#[N:24]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 896998123-Cyano-5-(pentafluoro-lambda6-sulphanyl)benzoic acidHCID 896999202-Amino-6-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenol

Product 1

HCID 896995883-Cyano-N-{2-hydroxy-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-lambda6-sulphanyl)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

74 mg (0.178 mmol, 70% pure) of the compound from Example 71A and 44 mg (0.160 mmol) of the compound of Example 23A were dissolved in 1 ml anhydrous DMF, and 81 mg (0.213 mmol) of HATU and 37 μl (0.213 mmol) of N,N-diisopropylethylamine were added in succession. The reaction mixture was stirred at RT for 30 min and then stirred into about 10 ml of water. The resulting precipitate was filtered off with suction, dissolved in about 3 ml of methanol and separated into its components by preparative HPLC (Method 33). The product fractions were combined and freed from the solvent. The residue obtained was triturated with a little dichloromethane at RT. Filtration with suction and drying of the solid under high vacuum gave 36 mg (37% of theory) of the title compound.

Workup

  1. filtrationThe resulting precipitate was filtered off with suction
  2. dissolutiondissolved in about 3 ml of methanol
  3. customseparated into its components by preparative HPLC (Method 33)
  4. customThe residue obtained
  5. customwas triturated with a little dichloromethane at RT
  6. filtrationFiltration with suction
  7. customdrying of the solid under high vacuum

Sources & evidence

ORD record
ord-34a03ea2335043e8a2a83cf7b0a0c7a8
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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