Water → 4-({(2S)-2-[(3-chlorophenoxy)methyl]pyrrolidin-1-yl}carbonyl)-N-1,3-thiazol-2-ylbenzenesulfonamide

HRID 401744노트

반응식

HRID 401744 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[Cl:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[O:22][CH2:23][C@@H:24]1[CH2:28][CH2:27][CH2:26][NH:25]1.[C:32](=O)([O-])[O-:33].[Na+].[Na+].O>Cl.C(=[Mo](=C=O)(=C=O)(=C=O)(=C=O)=C=O)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[O:22][CH2:23][C@@H:24]1[CH2:28][CH2:27][CH2:26][N:25]1[C:32]([C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1)=[O:33]

참가 물질

8

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10193184-Iodo-N-(thiazol-2-yl)benzenesulfonamideHCID 68534217(2S)-2-[(3-Chlorophenoxy)methyl]pyrrolidine hydrochloride

생성물 1

HCID 577319724-({(2S)-2-[(3-chlorophenoxy)methyl]pyrrolidin-1-yl}carbonyl)-N-1,3-thiazol-2-ylbenzenesulfonamide

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 178521658HCID 178521658, 화합물촉매HCID 313Hydrochloric Acid용매

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온도
110 °C

실험 절차

A mixture of 4-iodo-N-1,3-thiazol-2-ylbenzenesulfonamide (Preparation 98, 150 mg, 0.41 mmol), (2S)-2-(3-chloro-phenoxymethyl)-pyrrolidine hydrochloride (Preparation 90, 430 mg, 2.0 mmol), hexacarbonylmolybdenum (50 mg, 0.2 mmol), palladium(II) acetate (4 mg, 0.02 mmol), and sodium carbonate (130 mg, 1.2 mmol) in water (0.82 mL, 45 mmol) was heated 20 min at 110° C. in the microwave. The reaction mixture was diluted with 1 N HCl and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was taken up in 1.2 mL of DMSO, filtered, and purified via HPLC (Prep: Phenomenex 250×30.0 mm 15 micron C18 column. 40 mL/min. Gradient 15% B to 100% B over 25 min. Solvent A: 7800 water/200 acetonitrile/8 TFA. Solvent B: 7200 acetonitrile/800 water/8 TFA).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationfiltered
  7. custompurified via HPLC (Prep: Phenomenex 250×30.0 mm 15 micron C18 column. 40 mL/min. Gradient 15% B to 100% B over 25 min. Solvent A: 7800 water/200 acetonitrile/8 TFA. Solvent B: 7200 acetonitrile/800 water/8 TFA)

출처 및 근거

ORD 기록
ord-dc72073ce46d4fbc86ae40b01a14a287
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741934B2

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