Water → HCID 16035658, compound

HRID 2424437Notes

Reaction equation

HRID 2424437 reaction equation
[NH2:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])=[O:15])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:26][CH:27]([CH3:33])[CH2:28][CH2:29][C:30](O)=[O:31].CN(C)CCCN=C=NCC.O>O1CCCC1>[F:23][C:22]([F:25])([F:24])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:14]([N:11]1[CH2:10][CH2:9][N:8]([C:5]2[N:6]=[N:7][C:2]([NH:1][C:30](=[O:31])[CH2:29][CH2:28][CH:27]([CH3:33])[CH3:26])=[CH:3][CH:4]=2)[CH2:13][CH2:12]1)=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 12587Isocaproic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66849536[4-(6-Aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone

Product 1

HCID 16035658HCID 16035658, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of [4-(6-aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethyl-phenyl)methanone (0.226 g, 0.645 mmol) in tetrahydrofuran (10.0 mL) was added 4-methylpentanoic acid (0.500 g, 4.30 mmol) followed by (3-dimethylaminopropyl)-ethyl carbodiimide (1.0 mL). The mixture was stirred at ambient temperature overnight. Water was added and the mixture was extracted with ethyl acetate. The combined organic layer was dried with Na2SO4, concentrated, and the residue was dissolved again in a small amount of ethyl acetate. The solid, which precipitated by dropwise addition of hexane was filtered off and dried in vacuum to give the title product (0.070 g) as a white solid in 24% yield. 1H NMR (300 MHz, CDCl3) δ 9.15, 8.36, 7.74, 7.63, 7.56, 7.36, 7.05, 4.03-3.98, 3.93-3.89, 3.69-3.62, 3.55-3.53, 3.33-3.31, 2.51, 1.63-1.61, 0.91.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic layer was dried with Na2SO4
  3. concentrationconcentrated
  4. dissolutionthe residue was dissolved again in a small amount of ethyl acetate
  5. customThe solid, which precipitated by dropwise addition of hexane
  6. filtrationwas filtered off
  7. customdried in vacuum

Sources & evidence

ORD record
ord-0e33680d8fcb4e4fb973fecce1440a84
Source dataset
uspto-grants-2011_06
Patent number
US07964591B2

Reaction notes

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