Diisopropylethylamine → HCID 178434562, compound

HRID 522082

Reaction equation

HRID 522082 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([Cl:25])[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)=[CH:21][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[C:9]([C:18]([OH:20])=O)[CH:8]=1)=[O:5].[CH3:32][C:33]1[C:37]([NH2:38])=[CH:36][NH:35][N:34]=1.CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.CN(C(N(C)C)=[N+]1C2C(=NC=CC=2)[N+]([O-])=N1)C>CN(C=O)C>[Cl:1][C:2]1[CH:24]=[C:23]([Cl:25])[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)=[CH:21][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[C:9]([C:18]([NH:38][C:37]2[C:33]([CH3:32])=[N:34][NH:35][CH:36]=2)=[O:20])[CH:8]=1)=[O:5]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1184970355-(2,4-dichloro-5-(pyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acidHCID 178434557HCID 178434557, compoundHCID 178484293HCID 178484293, compound

Product 1

HCID 178434562HCID 178434562, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(2,4-dichloro-5-(pyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid (Example 111, 210 mg, 0.46 mmol), 3-methyl-1H-pyrazol-4-amine (68 mg, 0.69 mmol) and DIPEA (0.32 mL, 1.85 mmol) in anhydrous DMF (4 mL) was added 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (264 mg, 0.69 mmol). The reaction was stirred at room temperature for 1 hour under nitrogen. The reaction was partitioned between EtOAc (20 mL) and water (20 mL). The organic layer was collected, washed with brine (15 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by elution through an SCX-2 column using MeOH followed by 7N ammonia in MeOH, followed by purification using silica gel column chromatography eluting with EtOAc followed by 10% MeOH in DCM to afford the title compound (170 mg, 69%).

Workup

  1. customThe reaction was partitioned between EtOAc (20 mL) and water (20 mL)
  2. customThe organic layer was collected
  3. washwashed with brine (15 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by elution through an SCX-2 column
  8. customfollowed by purification
  9. washeluting with EtOAc

Sources & evidence

ORD record
ord-c553713fe9f2471fab68a2f3750d1598
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Linked notes

Loading…