Dimethylamine → HCID 66549234, compound

HRID 2174386Notes

Reaction equation

HRID 2174386 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:28]([F:31])([F:30])[F:29])[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:24][CH:23]([C:25]([OH:27])=O)[CH2:22]4)=[CH:17][CH:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].[CH3:32][N:33](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:34].F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CNC>CN(C=O)C.C1COCC1>[CH3:32][N:33]([CH3:34])[C:25]([CH:23]1[CH2:24][N:21]([C:18]2[CH:17]=[CH:16][C:15]([C:12]3[CH2:11][C:10]([C:4]4[CH:3]=[C:2]([Cl:1])[C:7]([Cl:8])=[C:6]([Cl:9])[CH:5]=4)([C:28]([F:31])([F:29])[F:30])[O:14][N:13]=3)=[CH:20][CH:19]=2)[CH2:22]1)=[O:27]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86707796HCID 86707796, compound

Product 1

HCID 66549234HCID 66549234, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1-{4-[5-(3,4,5-Trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-azetidine-3-carboxylic acid (Preparation 12, 0.1 g, 0.203 mmol) in DMF (3 mL) was added HATU (0.115 g, 0.304 mmol) HOBt (0.03 g, 0.223 mmol), DIPEA (0.052 g, 0.406 mmol) followed by addition of saturated solution of dimethyl amine in THF (2 mL) at 0° C. and stirred at 0° C. for 3 hours. After complete consumption of starting material, reaction mixture was quenched with water (20 mL), extracted with EtOAc (3×20 mL). Combined organic layer was washed with brine (50 mL), saturated solution of lithium chloride (50 mL), and water (50 mL), dried over sodium sulphate and evaporated in vacuo to get crude. Crude was purified by column chromatography on silica gel (100-200 mesh size). Compound was eluted using 0.6% methanol in DCM to afford white solid (0.050 g, 48%. 1H-NMR (400 MHz, CDCl3) δ: 2.94 (s, 3H), 2.97 (s, 3H), 3.61 (d, 1H, J=17.08 Hz), 3.69-3.77 (m, 1H), 4.02 (d, 1H, J=17.04 Hz), 4.11 (d, 4H, J=7.48 Hz), 6.40 (d, 2H, J=8.72 Hz), 7.46 (d, 2H, J=8.68 Hz), 7.63 (s, 2H); LC-MS (m/z): [M+H] 519.80.

Workup

  1. customAfter complete consumption of starting material, reaction mixture
  2. customwas quenched with water (20 mL)
  3. extractionextracted with EtOAc (3×20 mL)
  4. washCombined organic layer was washed with brine (50 mL), saturated solution of lithium chloride (50 mL), and water (50 mL)
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. customto get crude
  8. customCrude was purified by column chromatography on silica gel (100-200 mesh size)
  9. washCompound was eluted
  10. customto afford white solid (0.050 g, 48%

Sources & evidence

ORD record
ord-879cebe0fe684bd2913cd2a78908c896
Source dataset
uspto-grants-2015_06
Patent number
US09061013B2

Reaction notes

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