Diisopropylethylamine → N-{2,4-Dimethyl-5-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-[(trifluoromethyl)-sulphanyl]benzamide

HRID 1055756Notes

Reaction equation

HRID 1055756 reaction equation
C[C:2]1[C:8]([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)=[C:7]([CH3:23])[CH:6]=[CH:5][C:3]=1[NH2:4].[F:24][C:25]([S:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32](O)=[O:33])([F:27])[F:26].[CH3:38]N(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.C(#N)C>[CH3:38][C:5]1[CH:6]=[C:7]([CH3:23])[C:8]([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:2][C:3]=1[NH:4][C:32](=[O:33])[C:31]1[CH:35]=[CH:36][CH:37]=[C:29]([S:28][C:25]([F:27])([F:26])[F:24])[CH:30]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6883303-(Trifluoromethylthio)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89699939HCID 89699939, compound

Product 1

HCID 71667257N-{2,4-Dimethyl-5-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-[(trifluoromethyl)-sulphanyl]benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

80 mg (0.264 mmol) of the compound of Example 11A and 62 mg (0.277 mmol) of 3-[(trifluoromethyl)sulphanyl]benzoic acid were dissolved in 2 ml of DMF, and 120 mg (0.316 mmol) of HATU and 60 μl (0.343 mmol) of N,N-diisopropylethylamine were added in succession. After about 16 h of stirring at RT, the reaction mixture was diluted with 1 ml of acetonitrile and separated into its components by preparative HPLC (Method 36). Pooling of the product fractions, evaporation and drying under high vacuum gave 89 mg (95% pure, 63% of theory) of the title compound.

Workup

  1. customseparated into its components by preparative HPLC (Method 36)
  2. customPooling of the product fractions, evaporation
  3. customdrying under high vacuum

Sources & evidence

ORD record
ord-343d7bd50e86418aa5e2e97b7f6e3b74
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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