Hydrochloric Acid → HCID 57732189, 화합물

HRID 401745노트

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HRID 401745 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.C([C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](C)(C)[CH2:29][NH2:30])=[CH:23][CH:22]=1)(C)(C)C.[C:33](=[O:36])([O-])[O-].[Na+].[Na+].O.C(=O)([O-])[O-].[ClH:44]>C(=[Mo](=C=O)(=C=O)(=C=O)(=C=O)=C=O)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:44][C:21]1[CH:22]=[CH:23][C:24]([NH:27][CH2:28][CH2:29][NH:30][C:33](=[O:36])[C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]3[S:13][CH:14]=[CH:15][N:16]=3)(=[O:10])=[O:9])=[CH:4][CH:3]=2)=[CH:25][CH:26]=1

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 962WaterHCID 10340Sodium CarbonateHCID 19660Carbonate IonHCID 10193184-Iodo-N-(thiazol-2-yl)benzenesulfonamideHCID 68534592HCID 68534592, 화합물

생성물 1

HCID 57732189HCID 57732189, 화합물

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 178521658HCID 178521658, 화합물촉매

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온도
110 °C

실험 절차

A mixture of 4-iodo-N-1,3-thiazol-2-ylbenzenesulfonamide (Preparation 98, 0.2 g, 0.5 mmol), N-(2)-(4-tert-butyl-phenyl)-2-methyl-propane-1,2-diamine (0.55 g, 2.5 mmol), hexacarbonylmolybdenum (70 mg, 0.2 mmol), palladium(ii) acetate (6 mg, 0.02 mmol), and sodium carbonate (200 mg, 2 mmol) in water (1.5 mL, 83 mmol) was heated 30 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 dissolved in methylene chloride/MeOH and MP-Carbonate (2.73 mmol/g loading; 0.9 g, 2.50 mmol) was added. After stirring 1 h, LC/MS analysis indicated complete capture of the target compound. The resin was washed with methylene chloride then stirred in 8:1 methylene chloride/AcOH. LC/MS analysis indicated the target compound was released from the resin (not quantified). The mixture was filtered. The filtrate was concentrated in vacuo, and the residue was lyophilized from water/acetonitrile. The resulting solid was triturated with methylene chloride and ether. The resulting solid was 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. dissolutionThe residue was dissolved in methylene chloride/MeOH
  7. washThe resin was washed with methylene chloride
  8. stirringthen stirred in 8:1 methylene chloride/AcOH
  9. filtrationThe mixture was filtered
  10. concentrationThe filtrate was concentrated in vacuo
  11. customThe resulting solid was triturated with methylene chloride and ether
  12. customThe resulting solid was 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)

출처 및 근거

ORD 기록
ord-4f6c717d19e54aa89adc774c73c3a970
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741934B2

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