Triethylamine → tert-butyl ((4aR,11bR)-10-(5-(cyclopropylmethoxy)-3-methylpyrazine-2-carboxamido)-3,3,11b-trimethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate

HRID 627758Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627758
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:27][CH2:26][CH2:25][C@H:8]3[S:9](=[O:24])(=[O:23])[C:10]([CH3:22])([CH3:21])[C:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[N:12][C@:7]3([CH3:28])[C:6]=2[CH:29]=1.[CH:30]1([CH2:33][O:34][C:35]2[N:36]=[C:37]([CH3:44])[C:38]([C:41](O)=[O:42])=[N:39][CH:40]=2)[CH2:32][CH2:31]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.O.C([O-])(O)=O.[Na+]>[CH:30]1([CH2:33][O:34][C:35]2[N:36]=[C:37]([CH3:44])[C:38]([C:41]([NH:1][C:2]3[CH:3]=[CH:4][C:5]4[O:27][CH2:26][CH2:25][C@H:8]5[S:9](=[O:23])(=[O:24])[C:10]([CH3:22])([CH3:21])[C:11]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[N:12][C@:7]5([CH3:28])[C:6]=4[CH:29]=3)=[O:42])=[N:39][CH:40]=2)[CH2:31][CH2:32]1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 903014185-(Cyclopropylmethoxy)-3-methylpyrazine-2-carboxylic acidHCID 90307362tert-butyl ((4aR,11bR)-10-amino-3,3,11b-trimethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate

Produkt 1

HCID 131735340tert-butyl ((4aR,11bR)-10-(5-(cyclopropylmethoxy)-3-methylpyrazine-2-carboxamido)-3,3,11b-trimethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a solution of crude tert-butyl ((4aR,11bR)-10-amino-3,3,11b-trimethyl-4,4-dioxido-4a,5,6,11b-tetrahydro-3H-benzo[6,7]oxepino[4,5-b][1,4]thiazin-2-yl)carbamate (0.035 g, 0.083 mmol) in DCM (0.8 ml) were added 5-(cyclopropylmethoxy)-3-methylpyrazine-2-carboxylic acid (0.018 g, 0.087 mmol), triethylamine (0.023 ml, 0.165 mmol) and HATU (0.035 g, 0.091 mmol). The mixture was stirred at RT for 25 min. The reaction mixture was diluted with water and sat. NaHCO3, and extracted with DCM. The organic extract was washed with brine and dried over MgSO4. It was filtered and concentrated to give the crude material as a yellow oil which was used for next step directly. MS m/z: 614.1 [M+H].

Aufarbeitung

  1. extractionextracted with DCM
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationIt was filtered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c290b24813614e8ca4131dbfd1a48887
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309263B2

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