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Sodium triacetoxyborohydride → 5-(1-(3-(Methoxymethyl)-3-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)pyrrolidin-1-yl)ethyl)-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one

HRID 1045360
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1045360
[CH3:1][O:2][CH2:3][C:4]1([C:9]([N:11]2[CH2:20][CH2:19][C:18]3[N:17]=[CH:16][C:15]([C:21]([F:24])([F:23])[F:22])=[CH:14][C:13]=3[CH2:12]2)=[O:10])[CH2:8][CH2:7][NH:6][CH2:5]1.[C:25]([C:28]1[CH:39]=[CH:38][C:31]2[N:32]([CH3:37])[C:33](=[O:36])[N:34]([CH3:35])[C:30]=2[CH:29]=1)(=O)[CH3:26].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[CH3:1][O:2][CH2:3][C:4]1([C:9]([N:11]2[CH2:20][CH2:19][C:18]3[N:17]=[CH:16][C:15]([C:21]([F:22])([F:24])[F:23])=[CH:14][C:13]=3[CH2:12]2)=[O:10])[CH2:8][CH2:7][N:6]([CH:25]([C:28]2[CH:39]=[CH:38][C:31]3[N:32]([CH3:37])[C:33](=[O:36])[N:34]([CH3:35])[C:30]=3[CH:29]=2)[CH3:26])[CH2:5]1
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Komponenten

6

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 171392895-Acetyl-1,3-Dimethyl-1H-Benzo[D]Imidazol-2(3H)-OneHCID 59569566HCID 59569566, Verbindung

Produkt 1

HCID 441245565-(1-(3-(Methoxymethyl)-3-(3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-6-carbonyl)pyrrolidin-1-yl)ethyl)-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178460666
HCID 178460666, Verbindung
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The title compound was prepared according to general procedures described in Scheme 6: A mixture of (3-(methoxymethyl)pyrrolidin-3-yl)(3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone VIc (50 mg, 0.146 mmol), 5-acetyl-1,3-dimethyl-1H-benzo[d]imidazol-2(3H)-one (30 mg, 0.146 mmol) and Ti(OiPr)4 (51 mg, 0.182 mmol) in THF (2.5 mL) was irradiated in a Microwave instrument at 100° C. for 30 min (Personal Chemistry Emrys™ Optimizer microwave reactor). The reaction mixture was cooled and NaBH(OAc)3 (93 mg, 0.438 mmol) was added. The mixture was stirred at room temperature overnight. The solvent was removed in vacuo. The residue was dissolved in 30 mL of ethyl acetate and washed with sat. NaHCO3. The organic layer was washed with brine (×3), then dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by reverse phase preparative HPLC to yield the desired final product as trifluoroacetic salt with purity greater than 95% (18.0 mg, 23.2% yield): 1H NMR (300 MHz, CD3Cl3): δ 8.71 (s, 1H), 7.72 (s, 1H), 7.29 (bs, 1H), 7.01 (bs, 1H), 6.92 (s, 1H), 5.23 (m, 2H), 4.87 (m, 1H), 4.73 (m, 1H), 4.10-3.86 (m, 4H), 3.71 (m, 1H), 3.40 (m, 3H), 3.32-3.24 (m, 6H), 3.12 (m, 3H), 2.91 (bs, 1H), 2.66 (d, 1H), 2.42 (s, 1H), 2.30 (s, 1H), 1.81 (m, 2H); MS (ESI) m/z: Calculated for C27H32F3N5O3: 531.3. found: 532.0 (M+H)+.

Aufarbeitung

  1. customThe title compound was prepared
  2. customwas irradiated in a Microwave instrument at 100° C. for 30 min (Personal Chemistry Emrys™ Optimizer microwave reactor)
  3. temperatureThe reaction mixture was cooled
  4. customThe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in 30 mL of ethyl acetate
  6. washwashed with sat. NaHCO3
  7. washThe organic layer was washed with brine (×3)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was purified by reverse phase preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d8cbbe7a29d74211a963d8e3e56bcd55
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08569282B2

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