Hydrochloric Acid → 2-Methyl-2-({1-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylmethoxy]-naphthalene-2-carbonyl}-amino)-propionic acid methyl ester

HRID 2062068Notes

Reaction equation

HRID 2062068 reaction equation
[F:1][C:2]([F:27])([F:26])[CH2:3][O:4][C:5]1[N:10]=[CH:9][C:8]([CH2:11][O:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][C:14]=2[C:23](O)=[O:24])=[CH:7][CH:6]=1.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.[CH3:48][O:49][C:50](=[O:55])[C:51]([CH3:54])([CH3:53])[NH2:52].Cl>O.CN(C=O)C>[CH3:48][O:49][C:50](=[O:55])[C:51]([CH3:54])([NH:52][C:23]([C:14]1[CH:15]=[CH:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]=1[O:12][CH2:11][C:8]1[CH:9]=[N:10][C:5]([O:4][CH2:3][C:2]([F:27])([F:26])[F:1])=[CH:6][CH:7]=1)=[O:24])[CH3:53]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 13258034Methyl 2-aminoisobutyrate hydrochlorideHCID 667011311-[6-(2,2,2-Trifluoro-ethoxy)-pyridin-3-ylmethoxy]-naphthalene-2-carboxylic acid

Product 1

HCID 667010892-Methyl-2-({1-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylmethoxy]-naphthalene-2-carbonyl}-amino)-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

At 0° C. to 115 mg 1-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylmethoxy]-naphthalene-2-carboxylic acid in 2 mL of abs. DMF 82 mg EDC, 45 mg 1-hydroxybenzotriazole and 49 mg N,N-diisopropylethylamine were added. After 30 min at 0° C. 56 mg of 2,2-dimethylglycine methyl ester hydrochloride and 49 mg N,N-diisopropylethylamine were added. The mixture was stirred for 16 h at room temperature. The mixture was poured into cold water, acidified to pH 3 with 2M HCl, extracted with ethyl acetate, washed with sat. sodium hydrogen carbonate solution and brine, dried over magnesium sulphate, filtrated and concentrated in vacuo to provide 124 mg of 2-methyl-2-({1-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylmethoxy]-naphthalene-2-carbonyl}-amino)-propionic acid methyl ester.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with sat. sodium hydrogen carbonate solution and brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltrated
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5fa6476de784b34ba8059bdf840fdef
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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