Pyridine → N-[(5-bromo-1,3-thiazol-2-yl)carbamoyl]-2,6-dimethylbiphenyl-4-sulfonamide

HRID 252247

반응식

HRID 252247 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[C:4]([CH3:12])[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1.[O-:25][C:26]#[N:27].[Na+].Br.[Br:30][C:31]1[S:35][C:34]([NH2:36])=[N:33][CH:32]=1>C(#N)C.C(O)(=O)C.O>[Br:30][C:31]1[S:35][C:34]([NH:36][C:26]([NH:27][S:8]([C:6]2[CH:7]=[C:2]([CH3:1])[C:3]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:4]([CH3:12])[CH:5]=2)(=[O:10])=[O:9])=[O:25])=[N:33][CH:32]=1

참가 물질

8

반응물 4

HCID 1049PyridineHCID 517096Sodium CyanateHCID 27238485-Bromothiazol-2-amine monohydrobromideHCID 866167172,6-Dimethylbiphenyl-4-sulfonyl chloride

생성물 1

HCID 24752210N-[(5-bromo-1,3-thiazol-2-yl)carbamoyl]-2,6-dimethylbiphenyl-4-sulfonamide수율 9%

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

2,6-Dimethylbiphenyl-4-sulfonyl chloride (0.147 g, 0.53 mmol, 1.4 equiv.) and pyridine (0.152 ml, 1.87 mmol, 5.0 equiv.) were added to a stirred suspension of sodium cyanate (56 mg, 0.86 mmol, 2.3 equiv.) in dry acetonitrile (1.5 ml) and the mixture stirred at room temperature for 3 hours. 5-Bromo-thiazol-2-ylamine hydrobromide (97 mg, 0.38 mmol, 1.0 equiv.) was added and the reaction stirred for 1 hour. Water (2 ml) and acetic acid (3 drops) were added. The product was extracted into dichloromethane (2 ml), dried over sodium sulfate and evaporated to a brown gum. The gum was purified by preparative HPLC to give N-[(5-bromo-1,3-thiazol-2-yl)carbamoyl]-2,6-dimethylbiphenyl-4-sulfonamide, 15 mg (9% yield). LC @UV215 nm; Rt 2.64: 96%, m/z (ES+): 467, 468 (M+H).

후처리

  1. stirringthe reaction stirred for 1 hour
  2. extractionThe product was extracted into dichloromethane (2 ml)
  3. dry with materialdried over sodium sulfate
  4. customevaporated to a brown gum
  5. customThe gum was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-e60926281d7f4260a3e48e4d53bf8663
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868030B2

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