Pyridine → HCID 24752077, 화합물

HRID 252244노트

반응식

HRID 252244 반응식
[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[C:3]([S:7](Cl)(=[O:9])=[O:8])[CH:2]=1.N1C=CC=CC=1.[O-:18][C:19]#[N:20].[Na+].Cl.[NH2:23][C:24]1[S:25][C:26]([CH3:30])=[C:27]([CH3:29])[N:28]=1>C(#N)C.C(O)(=O)C.O>[CH3:29][C:27]1[N:28]=[C:24]([NH:23][C:19]([NH:20][S:7]([C:3]2[CH:4]=[CH:5][CH:6]=[C:1]([CH3:11])[CH:2]=2)(=[O:9])=[O:8])=[O:18])[S:25][C:26]=1[CH3:30]

참가 물질

8

반응물 4

HCID 1049PyridineHCID 517096Sodium CyanateHCID 27345953-Methylbenzenesulphonyl chlorideHCID 162113874,5-Dimethyl-1,3-thiazol-2-amine--hydrogen chloride (1/1)

생성물 1

HCID 24752077HCID 24752077, 화합물수율 55%

시약·촉매·용매 3

HCID 176Acetic Acid촉매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

m-Toluenesulfonyl chloride (0.076 ml, 0.53 mmol, 1.4 equiv.) and pyridine (0.103 ml, 1.27 mmol, 3.4 equiv.) were added to a stirred suspension of sodium cyanate (56 mg, 0.86 mmol, 2.3 equiv.) in dry acetonitrile (1 ml) and the mixture stirred at room temperature for 3 hours. 2-Amino-4,5-dimethylthiazole hydrochloride (34 mg, 0.28 mmol, 1.0 equiv.) was added and the reaction stirred for 1 hour. Water (2 ml) and acetic acid (3 drops) were added. The resulting precipitate was centrifuged for 10 minutes and the supernatant decanted. The solid washed with water (2 ml), the material centrifuged and supernatant decanted. The solid was dried under reduced pressure at 40° C. to give N-[(4,5-dimethyl-1,3-thiazol-2-yl)carbamoyl]-3-methylbenzenesulfonamide, 49 mg (55% yield). LC @UV215 nm; Rt 1.81: 93%, m/z (ES+): 326 (MH+), 651 (2 MH+); δH(400 MHz; d4-methanol) 7.54-7.98 (4H, m), 2.57 (3H, s), 2.31 (3H, s), 2.27 (3H, s).

후처리

  1. stirringthe reaction stirred for 1 hour
  2. waitThe resulting precipitate was centrifuged for 10 minutes
  3. washThe solid washed with water (2 ml)
  4. customThe solid was dried under reduced pressure at 40° C.

출처 및 근거

ORD 기록
ord-207d606a02e34799af541a953586ce46
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868030B2

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