Triethylamine → HCID 178448747, 화합물

HRID 536771노트

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HRID 536771 반응식
[C:1]([C:5]1[S:9][C:8](=[NH:10])[N:7]([CH2:11][CH2:12][CH2:13][CH3:14])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].O.N1(O)C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl:38][C:39]1[CH:40]=[CH:41][C:42]([F:48])=[C:43]([CH:47]=1)[C:44](O)=[O:45].C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:44](=[O:45])[C:43]2[CH:47]=[C:39]([Cl:38])[CH:40]=[CH:41][C:42]=2[F:48])/[N:7]([CH2:11][CH2:12][CH2:13][CH3:14])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

9

반응물 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27365375-Chloro-2-fluorobenzoic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 666433495-Tert-butyl-3-butyl-1,3,4-thiadiazol-2(3h)-imine

생성물 1

HCID 178448747HCID 178448747, 화합물

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

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온도
70 °C

실험 절차

To a mixture of Example 162C (250 mg, 1.17 mmol), 1H-benzo[d][1,2,3]triazol-1-ol hydrate (179 mg, 1.17 mmol), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (225 mg, 1.17 mmol), 5-chloro-2-fluorobenzoic acid (205 mg, 1.17 mmol) in 8 mL of THF was added triethylamine (163 μL, 1.17 mmol). The mixture was heated at 70° C. for 12 hours then cooled to ambient temperature and diluted with ethyl acetate and aqueous NaHCO3. The organic extract was concentrated and the residue was purified by chromatography on SiO2 using an Analogix® Intelliflash280™ (Hex-EtOAc, 0 to 30% gradient) to give the title compound. LC/MS m/z 369 (M+H)+.

후처리

  1. temperaturethen cooled to ambient temperature
  2. extractionThe organic extract
  3. concentrationwas concentrated
  4. customthe residue was purified by chromatography on SiO2 using an Analogix® Intelliflash280™ (Hex-EtOAc, 0 to 30% gradient)

출처 및 근거

ORD 기록
ord-c487aa13339245ae9e16ccaaa608ebc4
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859596B2

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