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Triethylamine → HCID 136121371, Verbindung

HRID 2079388
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2079388
[O:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[C:6]([OH:8])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:33][CH:34]1[CH2:39][CH2:38][N:37]([C:40]2[C:49]3[C:44](=[CH:45][C:46]([CH3:50])=[CH:47][CH:48]=3)[N:43]=[C:42]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=3[OH:57])[N:41]=2)[CH2:36][CH2:35]1.C(N(CC)CC)C>CN(C=O)C>[OH:57][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][C:51]=1[C:42]1[N:41]=[C:40]([N:37]2[CH2:36][CH2:35][CH:34]([NH:33][C:6]([C@H:2]3[CH2:3][CH2:4][CH2:5][O:1]3)=[O:8])[CH2:39][CH2:38]2)[C:49]2[C:44](=[CH:45][C:46]([CH3:50])=[CH:47][CH:48]=2)[N:43]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 2734707Tetrahydro-2-furoic acid, (+)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 136104957HCID 136104957, Verbindung

Produkt 1

HCID 136121371HCID 136121371, VerbindungAusbeute 42,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

(R)-Tetrahydrofuran-2-carboxylic acid (193 mg, 1.66 mmol) was dissolved in DMF (6 mL), followed by the addition of HATU (696 mg, 1.83 mmol). The mixture was then stirred for 15 min at room temperature under an N2 atmosphere. The 2-[4-(4-Amino-piperidin-1-yl)-7-methyl-quinazolin-2-yl]-phenol (556 mg, 1.66 mmol) was dissolved in DMF (8 mL) and added to the mixture, followed by triethylamine (336 mg, 0.463 mL, 3.32 mmol). After 30 min, theDMF was removed in vacuo and the crude product partitioned between water and ethyl acetate. The aqueous layer was separated, washed with ethyl acetate, and the combined organic layers dried over MgSO4, filtered, and concentrated to give crude product as an orange oil. Purification via silica gel chromatography (20% ethyl acetate/80% 1:1 CH2Cl2:hexane) gave pure (R)-Tetrahydro-furan-2-carboxylic acid {1-[2-(2-hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-piperidin-4-yl}-amide (303 mg, 42%). 1H NMR (400 MHz, DMSO-d6) δ 8.44 (dd, J=8.2, 1.5 Hz, 1H), 7.90 (d, J=8.5 Hz, 1H), 7.75 (d, J=8.3 Hz, 1H), 7.67 (s, 1H), 7.40-7.36 (m, 2H), 6.97-6.93 (m, 2H), 4.48-4.45 (m, 2H), 4.20 (dd, J=8.2, 5.3 Hz, 1H), 4.06-3.96 (m, 1H), 3.88 (dd, J=14.3, 6.6 Hz, 1H), 3.74 (dd, J=14.5, 6.7 Hz, 1H), 3.43-3.32 (m, 2H), 2.51 (s, 3H), 2.16-2.07 (m, 1H),

Aufarbeitung

  1. additionadded to the mixture
  2. waitAfter 30 min
  3. customtheDMF was removed in vacuo
  4. customthe crude product partitioned between water and ethyl acetate
  5. customThe aqueous layer was separated
  6. washwashed with ethyl acetate
  7. dry with materialthe combined organic layers dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give crude product as an orange oil
  11. customPurification via silica gel chromatography (20% ethyl acetate/80% 1:1 CH2Cl2:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b586d0a289754b63a2063619a4f2998d
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07928107B2

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