Hydrochloric Acid → HCID 178478761, Verbindung

HRID 424521Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 424521
[OH:1][CH2:2][CH2:3][N:4]([CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][S:17][C:16]2[CH:20]=[C:21]([NH:24][C:25]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[NH:26])[CH:22]=[CH:23][C:15]1=2)C(=O)OC(C)(C)C.[ClH:32]>CO>[ClH:32].[ClH:32].[OH:1][CH2:2][CH2:3][NH:4][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][S:17][C:16]2[CH:20]=[C:21]([NH:24][C:25]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)=[NH:26])[CH:22]=[CH:23][C:15]1=2

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 178453756HCID 178453756, Verbindung

Produkt 1

HCID 178478761HCID 178478761, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a solution of tert-butyl 2-hydroxyethyl(2-(7-(thiophene-2-carboximidamido)-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)carbamate (130 mg, 0.281 mmol) in MeOH (10 mL) was added 3N HCl (2.81 mL, 8.43 mmol). The yellow solution was heated at 75° C. for 30 minutes. At this time, the reaction was filtered and concentrated to half its volume. The yellow solution was then extracted with 2×50 mL CH2Cl2, and the aqueous layer was concentrated to dryness to give a yellow residue. This residue was dried under reduced (high vacuum) pressure to give compound 16 as yellow powder. 1H-NMR (CD3OD) δ 7.98-7.94 (m, 2H), 7.29 (pseudo t, J=4.2 Hz, 1H), 7.04-6.94 (m, 3H), 3.79 (brt, J=4.8 Hz, 2H), 3.72-3.65 (m, 4H), 3.28 (brs, 2H), 3.16 (brt, J=5.1 Hz, 2H), 3.09-3.06 (m, 2H); ESI-MS (m/z, %): 363 (MH+, free base, 100), 276 (90); ESI-HRMS calculated for C17H23N4O1S2 (MH+, free base): 363.1307, observed: 363.1316; HPLC purity: 96.2% a/a.

Aufarbeitung

  1. filtrationAt this time, the reaction was filtered
  2. concentrationconcentrated to half its volume
  3. extractionThe yellow solution was then extracted with 2×50 mL CH2Cl2
  4. concentrationthe aqueous layer was concentrated to dryness
  5. customto give a yellow residue
  6. customThis residue was dried

Quellen und Nachweise

ORD-Eintrag
ord-d1ca937a79424cad93bf8b815259cf79
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106043B2

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