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

HRID 1055758
Notes
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Reaction equation

HRID 1055758 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].[OH:24][C:25]([C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31](O)=[O:32])([CH3:27])[CH3:26].[CH3:37]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.C(=O)(O)[O-].C([O-])=O>CN(C=O)C.C(#N)C.CO>[CH3:37][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:31](=[O:32])[C:30]1[CH:34]=[CH:35][CH:36]=[C:28]([C:25]([OH:24])([CH3:27])[CH3:26])[CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 6

HCID 283FormateHCID 769Bicarbonate IonHCID 81531DiisopropylethylamineHCID 81671183-(1-Hydroxy-1-methylethyl)-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 89699666N-{2,4-Dimethyl-5-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-3-(2-hydroxypropan-2-yl)benzamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

250 mg (0.824 mmol) of the compound of Example 11A and 156 mg (0.865 mmol) of the compound of Example 92A were dissolved in 6.3 ml of DMF, and 376 mg (0.989 mmol) of HATU and 215 μl (1.24 mmol) of N,N-diisopropylethylamine were added in succession. After about 16 h of stirring at RT, the reaction mixture was diluted with about 3 ml of acetonitrile and then, in three portions, separated into its components by preparative HPLC (Method 36). After pooling and evaporation of the product fractions, the residue obtained was dissolved in a small amount of methanol and passed through a bicarbonate cartridge (from Polymerlabs, Stratospheres SPE, PL-HCO3 MP SPE, capacity 0.9 mmol) to prepare the free base from the formate salt from HPLC purification. Since the product obtained in this manner was still impure, it was purified further by MPLC (about 15 g of silica gel, mobile phase: cyclohexane/ethyl acetate/methanol 50:50:0→0:100:0→0:91:9). Evaporation of the product fractions and drying of the residue under high vacuum gave 238 mg (58% of theory, 95% pure) of the title compound.

Workup

  1. customin three portions, separated into its components by preparative HPLC (Method 36)
  2. customevaporation of the product fractions
  3. customthe residue obtained
  4. customfrom HPLC purification
  5. customSince the product obtained in this manner
  6. customit was purified further by MPLC (about 15 g of silica gel, mobile phase: cyclohexane/ethyl acetate/methanol 50:50:0→0:100:0→0:91:9)
  7. customEvaporation of the product fractions
  8. customdrying of the residue under high vacuum

Sources & evidence

ORD record
ord-1cbb60f8284847ad89410dba93b41378
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09394309B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes