Dimethylamine → HCID 66549043, compound

HRID 2174376Notes

Reaction equation

HRID 2174376 reaction equation
[F:1][C:2]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH2:19][C:18]([C:24]4[CH:29]=[C:28]([Cl:30])[C:27]([Cl:31])=[C:26]([Cl:32])[CH:25]=4)([C:20]([F:23])([F:22])[F:21])[O:17][N:16]=3)=[CH:11][CH:10]=2)[CH2:5][CH:4]([C:6]([OH:8])=O)[CH2:3]1.C(Cl)(=O)C(Cl)=O.[CH3:39][NH:40][CH3:41]>C(Cl)Cl.C1COCC1>[CH3:39][N:40]([CH3:41])[C:6]([CH:4]1[CH2:5][C:2]([F:1])([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH2:19][C:18]([C:24]4[CH:25]=[C:26]([Cl:32])[C:27]([Cl:31])=[C:28]([Cl:30])[CH:29]=4)([C:20]([F:23])([F:22])[F:21])[O:17][N:16]=3)=[CH:13][CH:14]=2)[CH2:3]1)=[O:8]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 65578Oxalyl chlorideHCID 86707793HCID 86707793, compound

Product 1

HCID 66549043HCID 66549043, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-fluoro-3-{4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-cyclobutanecarboxylic acid (Preparation 7, 0.085 g, 0.166 mmol) in DCM (4 mL) was added oxalyl chloride (0.025 g, 0.199 mmol) at 0° C. and stirred for 1 hour. After 1 hour, saturated solution of dimethyl amine in THF (4 mL) was added. Resulting reaction mixture was stirred at room temperature for 16 hours. After complete consumption of starting material, reaction mixture was concentrated in vacuo to afford crude. Crude was purified by column chromatography on silica gel (100-200 mesh size). Compound was eluted using 0.7% methanol in DCM to afford off white solid (0.026 g, 29%). 1H-NMR (400 MHz, CDCl3) δ: 2.72-2.78 (m, 2H), 2.87-2.92 (m, 1H), 2.94 (s, 3H), 2.98 (s, 3H), 2.99-3.09 (m, 2H), 3.68 (d, 1H, J=17.2 Hz), 4.08 (d, 1H, J=17.16 Hz), 7.54 (d, 2H, J=8.16 Hz), 7.64 (s, 2H), 7.70 (d, 2H, J=8.24 Hz); LC-MS (m/z): [M−H] 534.60.

Workup

  1. waitAfter 1 hour
  2. customResulting
  3. customreaction mixture
  4. stirringwas stirred at room temperature for 16 hours
  5. customAfter complete consumption of starting material, reaction mixture
  6. concentrationwas concentrated in vacuo
  7. customto afford crude
  8. customCrude was purified by column chromatography on silica gel (100-200 mesh size)
  9. washCompound was eluted

Sources & evidence

ORD record
ord-4defd1621a774fc3a8d234e0de2eb4f3
Source dataset
uspto-grants-2015_06
Patent number
US09061013B2

Reaction notes

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