Triethylamine → N-methyl-2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-(1,2,3,4-tetrahydro-2-methyl-1-naphthalenyl)-4-thiazolecarboxamide

HRID 2043771Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2043771
[CH3:1][NH:2][CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH:4]1[CH3:13].C(N(CC)CC)C.[CH3:21][C:22]1[N:26]([CH2:27][C:28]([N:30]2[CH2:35][CH2:34][CH:33]([C:36]3[S:37][CH:38]=[C:39]([C:41](Cl)=[O:42])[N:40]=3)[CH2:32][CH2:31]2)=[O:29])[N:25]=[C:24]([C:44]([F:47])([F:46])[F:45])[CH:23]=1>ClCCl>[CH3:1][N:2]([CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH:4]1[CH3:13])[C:41]([C:39]1[N:40]=[C:36]([CH:33]2[CH2:34][CH2:35][N:30]([C:28](=[O:29])[CH2:27][N:26]3[C:22]([CH3:21])=[CH:23][C:24]([C:44]([F:45])([F:47])[F:46])=[N:25]3)[CH2:31][CH2:32]2)[S:37][CH:38]=1)=[O:42]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 617508151,2,3,4-tetrahydro-N,2-dimethyl-1-naphthalenamineHCID 866377272-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarbonyl chloride2×

Produkt 1

HCID 66795996N-methyl-2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-(1,2,3,4-tetrahydro-2-methyl-1-naphthalenyl)-4-thiazolecarboxamideAusbeute 87,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 1,2,3,4-tetrahydro-N,2-dimethyl-1-naphthalenamine (115 mg, 0.66 mmol) and triethylamine (0.12 mL, 0.825 mmol) in 2 mL of dichloromethane was gradually added 2-[1-[[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-4-thiazolecarbonyl chloride (231 mg, 0.55 mmol) (i.e. the product of Example 19, Step D) at 0° C. The reaction mixture was stirred at room temperature for 16 h, diluted with 4 mL of dichloromethane, and washed with water, 1 N aqueous hydrochloric acid, water, saturated solution of sodium bicarbonate and brine. The filtered reaction mixture was dried over magnesium sulfate and concentrated in vacuo to give 270 mg of the title compound, the product of present invention as a white foam.

Aufarbeitung

  1. customat 0° C
  2. washwashed with water, 1 N aqueous hydrochloric acid, water, saturated solution of sodium bicarbonate and brine
  3. customThe filtered reaction mixture
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-df89526eaa55454f8afcaee03af2256b
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08586611B2

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