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

HRID 4138

반응식

HRID 4138 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-849b814f85c74b4ea52ba55f26ec47fb
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04723990

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