Hydrochloric Acid → HCID 66549427, compound

HRID 2174389Notes

Reaction equation

HRID 2174389 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[C:20]([Cl:24])=[C:19]([Cl:25])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[N:26]1[CH2:29][CH:28]([C:30]([OH:32])=O)[CH2:27]1.CCN=C=NCCCN(C)C.Cl.Cl.CCN(C(C)C)C(C)C.Cl.[F:56][C:57]([F:61])([F:60])[CH2:58][NH2:59]>CN(C=O)C>[F:56][C:57]([F:61])([F:60])[CH2:58][NH:59][C:30]([CH:28]1[CH2:29][N:26]([C:3]2[CH:4]=[CH:5][C:6]([C:8]3[CH2:12][C:11]([C:17]4[CH:22]=[C:21]([Cl:23])[C:20]([Cl:24])=[C:19]([Cl:25])[CH:18]=4)([C:13]([F:15])([F:16])[F:14])[O:10][N:9]=3)=[CH:7][C:2]=2[Cl:1])[CH2:27]1)=[O:32]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86707798HCID 86707798, compound

Product 1

HCID 66549427HCID 66549427, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1-{2-chloro-4-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-azetidine-3-carboxylic acid (Preparation 14, 0.1 g, 0.190 mmol) in dry DMF (3 mL) was added EDCl.HCl (0.055 g, 0.280 mmol), DIPEA (0.049 g, 0.380 mmol) and 2,2,2-trifluoro-ethylamine hydrochloride (0.026 g, 0.190 mmol) at 0° C. Resulting reaction mixture was stirred at room temperature for 18 hours under nitrogen atmosphere. After complete consumption of starting material, reaction mixture was quenched with water (50 mL), white solid was precipitated out, and solid was filtered, dried. Solid was purified by preparative TLC to afford off white solid (0.045 g, 41%). 1H-NMR (400 MHz, CDCl3) δ: 3.38-3.42 (m, 1H), 3.60 (d, 1H, J=17.08 Hz), 3.93-4.03 (m, 3H), 4.26-4.36 (m, 4H), 5.95 (t, 1H), 6.49 (d, 1H, J=8.52 Hz), 7.42 (dd, 1H, J1=8.56 Hz, J2=1.88 Hz), 7.47 (d, 1H, J=1.84 Hz), 7.62 (s, 2H); LC-MS (m/z): [M−H] 605.40.

Workup

  1. customat 0° C
  2. customResulting
  3. customreaction mixture
  4. customAfter complete consumption of starting material, reaction mixture
  5. customwas quenched with water (50 mL), white solid
  6. customwas precipitated out
  7. filtrationsolid was filtered
  8. customdried
  9. customSolid was purified by preparative TLC

Sources & evidence

ORD record
ord-6eb0adaac2ce41edb24c6a881a4fb097
Source dataset
uspto-grants-2015_06
Patent number
US09061013B2

Reaction notes

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