Ether hydrochloride → HCID 178479165, compound

HRID 510411Notes

Reaction equation

HRID 510411 reaction equation
O=[C:2]([CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[CH2:3][C:4]([O:6]CC)=O.[Cl:15][C:16]1[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:23][C:24]1[C:25]([NH2:30])=[N:26][NH:27][C:28]=1[NH2:29].CCOCC.Cl>C(O)(=O)C.CO>[ClH:15].[NH2:29][C:28]1[C:24]([CH2:23][C:17]2[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=2[Cl:15])=[C:25]2[N:30]=[C:2]([CH:9]3[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)[CH:3]=[C:4]([OH:6])[N:26]2[N:27]=1

Participants

6

Reactant 3

HCID 10953452Ether hydrochlorideHCID 23144053Ethyl 3-(oxan-4-yl)-3-oxopropanoateHCID 71270938HCID 71270938, compound

Product 1

HCID 178479165HCID 178479165, compoundYield 51.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a mixture of ethyl 3-oxo-3-(tetrahydro-2H-pyran-4-yl)propanoate (0.100 g, 0.498 mmol) and 4-[(2,3-dichlorophenyl)methyl]-1H-pyrazole-3,5-diamine (0.128 g, 0.498 mmol) was added in Acetic Acid (2 mL). The reaction vessel was subjected to MW irradiation at 100° C. for 40 min then 70° C. for 180 min. The mixture was concentrated. The residue was purified by reversed phase HPLC (25% CH3CN (0.1% TFA)/Water (0.1% TFA)) and then repurified (10˜50% CH3CN (0.1% TFA)/Water (0.1% TFA) to give the product. 1 M ether/HCl (3 mL) was added to the solution of the product in MeOH (10 mL). The mixture was stirred for 3 h. The solvent was removed to give the titled product as solid (55 mg, 27%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.53-1.84 (m, 4H) 2.63-2.83 (m, 1H) 3.22-3.46 (m, 2H) 3.93 (m, 2H) 4.01 (s, 2H) 5.63 (s, 1H) 6.90 (d, J=7.07 Hz, 1H) 7.25 (t, J=7.96 Hz, 1H) 7.43-7.59 (m, 1H) 11.92 (br. s., 1H). LC/MS: MS (ES+) m/e 393.0 [M+H]+.

Workup

  1. customThe reaction vessel was subjected to MW irradiation at 100° C. for 40 min
  2. concentrationThe mixture was concentrated
  3. customThe residue was purified by reversed phase HPLC (25% CH3CN (0.1% TFA)/Water (0.1% TFA))
  4. customrepurified (10˜50% CH3CN (0.1% TFA)/Water (0.1% TFA)
  5. customto give the product
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-6ac4be5db9054177971aa4abca67853a
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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