Hydrochloric Acid → HCID 11691851, compound

HRID 1452706Notes

Reaction equation

HRID 1452706 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([OH:33])([C:29]([F:32])([F:31])[F:30])[C:25]([F:28])([F:27])[F:26])[CH:19]=1.[CH3:34][NH:35][CH3:36].Cl.CN1CCOCC1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl.O>[CH3:34][N:35]([CH3:36])[C:11](=[O:12])[C:10]1[CH:9]=[CH:8][C:7]([C:5]2[O:6][C:2]([CH3:1])=[C:3]([CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([OH:33])([C:25]([F:27])([F:28])[F:26])[C:29]([F:31])([F:30])[F:32])[CH:19]=3)[N:4]=2)=[CH:15][CH:14]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 11576497HCID 11576497, compound

Product 1

HCID 11691851HCID 11691851, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 25 mg (0.05 mmol) of 4-{5-methyl-4-[3-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxymethyl]-oxazol-2-yl}-benzoic acid (example 81) in 1.5 ml of CH2Cl2 were added 8.6 mg (0.11 mol) of dimethylamine.HCl and 23 μl (0.11 mmol) of NMM. The solution was cooled to 0° C. and 13.1 mg (0.07 mmol, 1.3 eq) of EDCI and 1.4 mg (0.01 mmol) of HOBT were added. The mixture was stirred at room temperature overnight. Water was added and the inorganic phase was extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated. Column chromatography with CH2Cl2/MeOH 98:2 gave 22 mg (83%) N,N-dimethyl-4-{5-methyl-4-[3-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxymethyl]-oxazol-2-yl}-benzamide as a colorless oil, MS: 501 (M−H)−.

Workup

  1. extractionthe inorganic phase was extracted with EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-0b55cd6247b44395924ca3029d338015
Source dataset
uspto-grants-2009_01
Patent number
US07473705B2

Reaction notes

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