Triethylamine → 4-oxo-4-(1-thien-2-yl-3,4-dihydroisoquinolin-2(1H)-yl)-N-(3-(trifluoromethyl)benzyl)butyric acid amide

HRID 383995

Reaktionsgleichung

Reaktionsgleichung von HRID 383995
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][NH:7]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.[O:47]=[C:48]([NH:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[C:58]([C:62]([F:65])([F:64])[F:63])[CH:57]=1)[CH2:49][CH2:50][C:51](O)=[O:52]>C1COCC1>[O:52]=[C:51]([N:7]1[CH2:8][CH2:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]1[C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH2:50][CH2:49][C:48]([NH:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[C:58]([C:62]([F:63])([F:64])[F:65])[CH:57]=1)=[O:47]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 27936431-(Thiophen-2-yl)-1,2,3,4-tetrahydroisoquinolineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 433971044-Oxo-4-(3-(trifluoromethyl)benzylamino)butyric acid

Produkt 1

HCID 468297104-oxo-4-(1-thien-2-yl-3,4-dihydroisoquinolin-2(1H)-yl)-N-(3-(trifluoromethyl)benzyl)butyric acid amideAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

236 mg (1.1 mmol) of 1-(thiophen-2-yl)-1,2,3,4-tetrahydroisoquinoline, 380 mg (1.0 mmol) of HATU and 263 μl (1.9 mmol) of NEt3 were added in succession to a solution of 275 mg (1.0 mmol) of 4-oxo-4-(3-(trifluoromethyl)benzylamino)butyric acid (intermediate VVV01) in THF (8 ml) and the mixture was then stirred for 24 h at RT. Then it was diluted with EE (30 ml) and washed twice with a 4M aqueous NH4Cl solution and with a 1M aqueous NaHCO3 solution. The organic phase was dried over MgSO4, filtered and concentrated to small volume under vacuum. Column chromatography (EE) of the residue produced 410 mg (0.87 mmol, 87%) of 4-oxo-4-(1-thien-2-yl-3,4-dihydroisoquinolin-2(1H)-yl)-N-(3-(trifluoromethyl)benzyl)butyric acid amide. MS: m/z 473.1 [M+H]+.

Aufarbeitung

  1. additionThen it was diluted with EE (30 ml)
  2. washwashed twice with a 4M aqueous NH4Cl solution and with a 1M aqueous NaHCO3 solution
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to small volume under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0243b347ac7f47c39ca3b66c7569ab93
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367700B2

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