4-(3-(Pyrrolidin-1-yl)propyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine → HCID 178511899, Verbindung

HRID 1917198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1917198
[N:1]1([CH2:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][S:12][C:11]3[CH:15]=[C:16]([NH2:19])[CH:17]=[CH:18][C:10]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.I.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26](SC)=[NH:27]>C(O)C.C([O-])(O)=O.[Na+]>[N:1]1([CH2:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][S:12][C:11]3[CH:15]=[C:16]([NH:19][C:26]([C:22]4[S:21][CH:25]=[CH:24][CH:23]=4)=[NH:27])[CH:17]=[CH:18][C:10]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 591440974-(3-(Pyrrolidin-1-yl)propyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amineHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Produkt 1

HCID 178511899HCID 178511899, VerbindungAusbeute 85,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A solution of 4-(3-(pyrrolidin-1-yl)propyl)-3,4-dihydro-2H-benzo[b][1,4]thiazin-7-amine (0.43 g, 1.550 mmol) in dry ethanol (15 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.884 g, 3.10 mmol) at room temperature, and the resulting mixture was stirred overnight (18 hours). The reaction was diluted with saturated NaHCO3 solution (30 mL), and the product was extracted into CH2Cl2 (3×20 mL). The combined CH2Cl2 layers were washed with brine (20 mL) and then dried (Na2SO4). The solvent was evaporated, and the crude material was purified by column chromatography (5:95 (2 M NH3 in MeOH):CH2Cl2), to obtain the title product 21 (0.51 g, 85%) as a solid. 1H NMR (DMSO-d6) δ 7.68 (d, 1H, J=4.5 Hz), 7.55 (d, 1H, J=5.1 Hz), 7.06 (dd, 1H, J=3.6, 4.9 Hz), 6.70 (d, 1H, J=8.7 Hz), 6.52-6.44 (m, 2H), 6.32 (brs, 2H), 3.51-3.48 (m, 2H), 3.27 (t, 2H, J=7.2 Hz), 3.04-3.00 (m, 2H), 2.48-2.40 (m, 6H), 1.80-1.60 (m, 6H); ESI-MS (m/z, %): 387 (MH+, 68), 276 (100), 194 (75); HPLC purity: 98.32% by area.

Aufarbeitung

  1. extractionthe product was extracted into CH2Cl2 (3×20 mL)
  2. washThe combined CH2Cl2 layers were washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was evaporated
  5. customthe crude material was purified by column chromatography (5:95 (2 M NH3 in MeOH):CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-d0fec40cf9134a52b3e7ed76bdc9aaf4
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618286B2

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