Diisopropylethylamine → US12358901, Example RE6

HRID 1484667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1484667
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.CCN(C(C)C)C(C)C.[CH3:22][C:23]1[C:28]2[O:29][CH2:30][C:31]3([CH2:33][CH2:32]3)[C:27]=2[C:26]([O:34][C:35]2[N:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=2)=[CH:25][CH:24]=1.Cl.[NH2:43][C:44]([CH3:50])([CH3:49])[C:45](OC)=[O:46]>C(Cl)Cl>[CH3:50][C:44]1([CH3:49])[NH:43][C:2](=[O:4])[N:41]([C:38]2[CH:39]=[N:40][C:35]([O:34][C:26]3[C:27]4[C:31]5([CH2:30][O:29][C:28]=4[C:23]([CH3:22])=[CH:24][CH:25]=3)[CH2:33][CH2:32]5)=[CH:36][CH:37]=2)[C:45]1=[O:46]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 13258034Methyl 2-aminoisobutyrate hydrochlorideHCID 679599396-(7-methylspiro[2H-benzofuran-3,1'-cyclopropane]-4-yl)oxypyridin-3-amine2×

Produkt 1

HCID 57411298US12358901, Example RE6

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To a solution of triphosgene (30 mg, 0.1 mmol) in dry DCM (1 ml) at 0° C., under nitrogen atmosphere, DIPEA (0.175 ml, 1.0 mmol) was added followed by the addition (slowly added) of a solution of 6-(7-methylspiro[2H-benzofuran-3,1′-cyclopropane]-4-yl)oxypyridin-3-amine (Intermediate 15, 27 mg, 0.1 mmol) in dry DCM (2 ml) and the reaction mixture was stirred for 15 minutes at the same temperature. After that a solution of Methyl 2-amino-2-methylpropanoate hydrochloride (30 mg, 0.2 mmol) in dry DCM (2 ml) was added and the reaction mixture was stirred for 30 minutes at 0° C. The reaction was quenched with a 1M aqueous solution of HCl (5 ml), diluted with DCM (10 ml) and two phases were separated. The organic layer was washed with brine (10 ml), dried (Na2SO4), filtered and evaporated affording the urea intermediate as yellow foam.

Aufarbeitung

  1. additionfollowed by the addition (
  2. stirringthe reaction mixture was stirred for 30 minutes at 0° C
  3. customThe reaction was quenched with a 1M aqueous solution of HCl (5 ml)
  4. additiondiluted with DCM (10 ml) and two phases
  5. customwere separated
  6. washThe organic layer was washed with brine (10 ml)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-bedc80143f3446dfac04e9c755af7b32
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422272B2

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