Tetrahydrofuran → HCID 25211504, Verbindung

HRID 572297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 572297
[CH3:1][C:2]1[C:3]([C:11]2[S:15][C:14]([C:16]([OH:18])=O)=[CH:13][CH:12]=2)=[N:4][O:5][C:6]=1[C:7]([F:10])([F:9])[F:8].NC1C=CN=CC=1Cl.C1COCC1.[N:32]12[CH2:40][CH2:39][CH2:38][C@H:37]1[CH2:36][NH:35][CH2:34][CH2:33]2>C(N(CC)CC)C>[CH2:36]1[N:35]([C:16]([C:14]2[S:15][C:11]([C:3]3[C:2]([CH3:1])=[C:6]([C:7]([F:8])([F:9])[F:10])[O:5][N:4]=3)=[CH:12][CH:13]=2)=[O:18])[CH2:34][CH2:33][N:32]2[CH2:40][CH2:39][CH2:38][C@@H:37]12

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 5818533-Chloropyridin-4-amineHCID 781249(6S)-1,4-Diazabicyclo(4.3.0)nonaneHCID 252109975-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid

Produkt 1

HCID 25211504HCID 25211504, VerbindungAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Prepared from 5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid and 4-amino-3-chloropyridine by the method described in Example 2 Method B reversing the order of addition such that solid acid chloride was added to a THF solution of triethylamine and (S)-1,4-diazabicyclo[4.3.0]nonane. The reaction mixture was evaporated to a solid, triturated and filtered with the aid of water, then washed with a saturated aqueous NaHCO3 solution followed by water to afford product as a yellow colored solid (82 mg, 85%). 1H NMR (CDCl3) 1.34-1.48 (m, 1H), 1.70-1.90 (m, 3H), 1.92-2.20 (m, 1H), 2.10-2.26 (m, 2H), 2.32 (d, J=1.3, 3H), 2.80 (br s, 1H), 3.03-3.11 (m, 2H), 3.20 (obs br s, 1H), 4.40 (br s, 2H), 7.29 (d, J=4.0, 1H), 7.41 (d, J=3.5, 1H). 13C NMR 7.9, 21.3, 27.5, 30.0, ˜48 (br), 51.8, 53.5, 62.8, 114.7, 118.7 (q, J=271), 128.0, 129.3, 131.2, 140.2, 155.2 (q, J=40), 157.9, 162.9. 19F NMR −63.1. LC/MS 4.34 min, [M+1]+ 386.

Aufarbeitung

  1. customThe reaction mixture was evaporated to a solid
  2. customtriturated
  3. filtrationfiltered with the aid of water
  4. washwashed with a saturated aqueous NaHCO3 solution

Quellen und Nachweise

ORD-Eintrag
ord-2cf77f2177ec4f02948295fa0dccf662
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029397B2

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