Diisopropylethylamine → methyl (R)-3-((2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxamido)methyl)-5-methoxybenzoate

HRID 59909

Reaktionsgleichung

Reaktionsgleichung von HRID 59909
[CH2:1]([O:3][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[N:18]=[CH:17][C:16]([C:19](O)=[O:20])=[CH:15][N:14]=2)[CH2:8]1)[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.Cl.[NH2:60][CH2:61][C:62]1[CH:63]=[C:64]([CH:69]=[C:70]([O:72][CH3:73])[CH:71]=1)[C:65]([O:67][CH3:68])=[O:66]>ClCCl>[CH2:1]([O:3][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[N:18]=[CH:17][C:16]([C:19]([NH:60][CH2:61][C:62]3[CH:63]=[C:64]([CH:69]=[C:70]([O:72][CH3:73])[CH:71]=3)[C:65]([O:67][CH3:68])=[O:66])=[O:20])=[CH:15][N:14]=2)[CH2:8]1)[CH3:2]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118366221(R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acidHCID 118366264Methyl 3-(aminomethyl)-5-methoxybenzoate hydrochloride

Produkt 1

HCID 131737072methyl (R)-3-((2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxamido)methyl)-5-methoxybenzoateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acid (50 mg, 0.14 mmol) and HATU (63 mg, 0.17 mmol) in dry dichloromethane (3 mL) was added N,N-diisopropylethylamine (0.075 mL, 0.42 mmol) at 20-25° C. The mixture was stirred for 10 min, then methyl 3-(aminomethyl)-5-methoxybenzoate hydrochloride was added (33 mg, 0.14 mmol) at 20-25° C. The reaction mixture was stirred at 20-25° C. for 1 hour. The mixture was concentrated under reduced pressure and the resulting residue was dissolved in ethyl acetate (10 mL), washed with water (2 times with 10 mL), and dried over NaSO4. The organics were concentrated under reduced pressure to obtain methyl (R)-3-((2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxamido)methyl)-5-methoxybenzoate (65 mg, 87%).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at 20-25° C. for 1 hour
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe resulting residue was dissolved in ethyl acetate (10 mL)
  4. washwashed with water (2 times with 10 mL)
  5. dry with materialdried over NaSO4
  6. concentrationThe organics were concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-46abd95da3f147deb299b0b480716d06
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440949B2

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