Pyrrolidine → 2-(1-Pyrrolidinylmethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide, hydrochloride salt

HRID 4138

Reaktionsgleichung

Reaktionsgleichung von HRID 4138
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH:12][C:13]([NH:15][C:16]1[N:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[N:17]=1)=[O:14])(=[O:11])=[O:10].[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.[K+].[Br-]>CN(C)C=O>[ClH:1].[N:26]1([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[S:9]([NH:12][C:13]([NH:15][C:16]2[N:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[N:17]=2)=[O:14])(=[O:11])=[O:10])[CH2:30][CH2:29][CH2:28][CH2:27]1

Komponenten

5

Edukt 3

HCID 31268PyrrolidineHCID 253877Potassium BromideHCID 133646172-(Chloromethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)-aminocarbonyl]benzenesulfonamide

Produkt 1

HCID 133646192-(1-Pyrrolidinylmethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide, hydrochloride salt

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A slurry of 2-(chloromethyl)-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]benzenesulfonamide (1.00 g) in dimethylformamide (5 ml) was contacted with pyrrolidine (0.45 ml) and stirred for 3.5 hrs. Volatiles were removed under vacuum and the residue was taken up in methanol. Solvent was removed and the water (15 ml) was added and the pH was adjusted to 6.0 by addition of dilute hydrochloric acid. Cooling and scratching produced a white solid which was collected and dried to give 488 mg, m.p. 117°-123°. A 400 mg sample was crystallized from acetonitrile to give 269 mg. m.p. 132°-134° C. 1H nmr δCDCl3TMS 13.0-11.0 (brds 2H), 8.63 (s, 1 NH), 8.37-8.20, 8.05-7.90, and 7.70-7.33 (m, 4H), 5.68 (s, 1H), 5.00 (s, 2H), 3.90 (s, 6H), 3.70-2.90 (m, 4H), 2.30-1.90 (m, 4H). IR (KBr) 3650-2200, 1710, 1610, 1580, 1450, 1360, 1200, 1165 are major absorption bands.

Aufarbeitung

  1. customVolatiles were removed under vacuum
  2. customSolvent was removed
  3. additionthe water (15 ml) was added
  4. additionthe pH was adjusted to 6.0 by addition of dilute hydrochloric acid
  5. temperatureCooling
  6. customscratching produced a white solid which
  7. customwas collected
  8. customdried
  9. customto give 488 mg, m.p. 117°-123°
  10. customA 400 mg sample was crystallized from acetonitrile
  11. customto give 269 mg
  12. customabsorption bands

Quellen und Nachweise

ORD-Eintrag
ord-849b814f85c74b4ea52ba55f26ec47fb
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04723990

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