Triethylamine → HCID 178523078, compound

HRID 522077Notes

Reaction equation

HRID 522077 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([Cl:25])[C:22]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[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](O)=[O:19])[CH:8]=1)=[O:5].Cl.[NH:34]1[C:38]([CH2:39][NH2:40])=[CH:37][N:36]=[N:35]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C)C=O>[NH3:6].[NH:34]1[C:38]([CH2:39][NH:40][C:18]([C:9]2[CH:8]=[C:7]([NH:6][C:4](=[O:5])[C:3]3[CH:21]=[C:22]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][N:27]=4)[C:23]([Cl:25])=[CH:24][C:2]=3[Cl:1])[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:10]=2)=[O:19])=[CH:37][N:36]=[N:35]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1184970945-(2,4-dichloro-5-(5-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acidHCID 178479188HCID 178479188, compound

Product 2

HCID 222AmmoniaHCID 178523078HCID 178523078, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(2,4-dichloro-5-(5-fluoropyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid (Example 102, 100 mg, 0.212 mmol), (1H-1,2,3-triazol-5-yl)methanamine hydrochloride (43 mg, 0.32 mmol) and HATU (121 mg, 0.32 mmol) were dissolved in dimethylformamide (5 mL) under nitrogen. Triethylamine (0.12 mL, 0.85 mmol) was added dropwise and the reaction stirred at room temperature for 1 hour. The reaction was concentrated in vacuo. The residue was partitioned between ethyl acetate (50 mL) and water (50 mL), the organic layer was collected, dried over magnesium sulphate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 95:5:0.5 dichloromethane:methanol:ammonia to afford the title compound as a white solid (48 mg, 42%).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate (50 mL) and water (50 mL)
  3. customthe organic layer was collected
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with 95:5:0.5 dichloromethane

Sources & evidence

ORD record
ord-5b2ecb014f904c99ab6d69b6c1cac20e
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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