Dimethylformamide → HCID 136348444, Verbindung

HRID 1748775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748775
[CH2:1]([N:3]1[C:7]2[NH:8][CH2:9][CH2:10][S:11][CH:12]([C:13]3[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][C:14]=3[CH3:22])[C:6]=2[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[N:4]1)[CH3:2].S(Cl)([Cl:31])=O.CN(C=O)C>C(Cl)Cl>[CH2:1]([N:3]1[C:7]2[NH:8][CH2:9][CH2:10][S:11][CH:12]([C:13]3[CH:21]=[CH:20][C:16]([C:17]([Cl:31])=[O:18])=[CH:15][C:14]=3[CH3:22])[C:6]=2[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[N:4]1)[CH3:2]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 136348443HCID 136348443, Verbindung

Produkt 1

HCID 136348444HCID 136348444, VerbindungAusbeute 100,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a mixture of 4-(1-ethyl-3-(pyridin-2-yl)-4,6,7,8-tetrahydro-1H-pyrazolo[3,4-e][1,4]thiazepin-4-yl)-3-methylbenzoic acid (2.0 g, 5.07 mmol, Preparation #V.1) and thionyl chloride (1.8 mL, 25.3 mmol) in DCM (20 mL) was added DMF (0.04 mL, 0.51 mmol) and stirred at about 50° C. for about 2 h. The reaction was cooled to ambient temperature and the solvent was removed under reduced pressure to give 4-(1-ethyl-3-(pyridin-2-yl)-4,6,7,8-tetrahydro-1H-pyrazolo[3,4-e][1,4]thiazepin-4-yl)-3-methylbenzoyl chloride (2.1 g, 5.09 mmol, 100%) as a brown solid. LC-MS (Table 1, Method k) Rt=1.97 min, m/z 409 (M+H)+ for MeOH quench.

Aufarbeitung

  1. temperatureThe reaction was cooled to ambient temperature
  2. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-47bdd204154a4c9ab285259d32c39d2c
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150592B2

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