1,2-Dichloroethane → HCID 86679596, Verbindung

HRID 1776653Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1776653
[CH3:1][S:2]([NH:5][C:6]1[N:11]=[CH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8][N:7]=1)(=[O:4])=[O:3].[Cl:15][C:16]1[CH:17]=[N+:18]([O-:45])[CH:19]=[C:20]([Cl:44])[C:21]=1[CH2:22][C@@H:23]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH:36]([F:38])[F:37])=[C:31]([O:39][CH2:40][CH:41]2[CH2:43][CH2:42]2)[CH:30]=1)[O:24][C:25](=[O:28])[CH2:26]O.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:44][C:20]1[CH:19]=[N+:18]([O-:45])[CH:17]=[C:16]([Cl:15])[C:21]=1[CH2:22][C@@H:23]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH:36]([F:38])[F:37])=[C:31]([O:39][CH2:40][CH:41]2[CH2:43][CH2:42]2)[CH:30]=1)[O:24][C:25](=[O:28])[CH2:26][O:13][C:12]([C:9]1[CH:8]=[N:7][C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[N:11][CH:10]=1)=[O:14]

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 86679512(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-hydroxyacetoxy)ethyl)pyridine 1-oxideHCID 866795972-(Methylsulfonamido)pyrimidine-5-carboxylic acid

Produkt 1

HCID 86679596HCID 86679596, VerbindungAusbeute 45,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 2-(methylsulfonamido)pyrimidine-5-carboxylic acid (0.130 g, 0.599 mmol) in dry DCM (5.44 ml), (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-hydroxyacetoxy)ethyl)pyridine 1-oxide (See Scheme 21, step 6-9) (0.260 g, 0.544 mmol), EDC (0.313 g, 1.632 mmol), and DMAP (0.665 g, 0.544 mmol) were sequentially added with stirring at room temperature under nitrogen, and the mixture was stirred for 20 hours. The solvent was removed, and the crude was purified by flash chromatography on silica gel column (DCM:MeOH=97:3 to 95:5) affording (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(2-(methylsulfonamido)pyrimidine-5-carbonyloxy)acetoxy)ethyl)pyridine 1-oxide as a pale yellow spongy solid (0.168 g, 0.248 mmol, 45.6% yield, MS/ESI+ 677.1 [MH]+, [αD]=−47.48, c=0.5, MeOH).

Aufarbeitung

  1. additionwere sequentially added
  2. stirringthe mixture was stirred for 20 hours
  3. customThe solvent was removed
  4. customthe crude was purified by flash chromatography on silica gel column (DCM:MeOH=97:3 to 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-99c7c3f88e5146fdb8ac66515e294c41
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09265768B2

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