Triethylamine → HCID 178448747、化合物

HRID 536771ノート

反応式

HRID 536771 の反応式
[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]

参加物

9

反応物 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

生成物 1

HCID 178448747HCID 178448747、化合物

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
70 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-c487aa13339245ae9e16ccaaa608ebc4
出典データセット
uspto-grants-2014_10
特許番号
US08859596B2

反応ノート

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