Cesium carbonate → HCID 25109829, 화합물

HRID 505559

반응식

HRID 505559 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:19]3[N:18]=[N:17][NH:16][C:15]=3[CH:14]=[CH:13][C:12]=2[Cl:20])[CH:9]=1)[C:5]#[N:6].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:28][C:29]1[O:30][C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[N:32][N:33]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:19]3[C:15](=[N:16][N:17]([CH2:28][C:29]4[O:30][C:31]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)=[N:32][N:33]=4)[N:18]=3)[CH:14]=[CH:13][C:12]=2[Cl:20])[CH:9]=1)[C:5]#[N:6]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 3149412-(Chloromethyl)-5-phenyl-1,3,4-oxadiazoleHCID 178509930HCID 178509930, 화합물

생성물 1

HCID 25109829HCID 25109829, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3-chloro-5-[(5-chloro-1H-1,2,3-benzotriazol-4-yl)oxy]benzonitrile (100 mg, 0.328 mmol), cesium carbonate (107 mg, 0.328 mmol) and 2-(chloromethyl)-5-phenyl-1,3,4-oxadiazole (64 mg, 0.328 mmol) were combined and suspended in DMF (2 mL). After 16 hours, the reaction mixture was quenched with saturated aqueous ammonium chloride (1 mL) and extracted with EtOAc (2×25 mL). The combined organic fractions were evaporated under reduced pressure. The resulting residue was purified by reverse phase chromatography eluting with 30-95% MeCN/H2O+0.1% TFA. The product fractions were concentrated to yield the title compound. 1H NMR (DMSO-d6) δ 8.01 (d, J=9.1 Hz, 1H) 7.92 (d, J=8.6 Hz, 2H), 7.72 (m, 1H), 7.68 (m, 1H), 7.60 (m, 5H), 6.50 (s, 1H). HRMS (M+1)=463.0464.

후처리

  1. customthe reaction mixture was quenched with saturated aqueous ammonium chloride (1 mL)
  2. extractionextracted with EtOAc (2×25 mL)
  3. customThe combined organic fractions were evaporated under reduced pressure
  4. customThe resulting residue was purified by reverse phase chromatography
  5. washeluting with 30-95% MeCN/H2O+0.1% TFA
  6. concentrationThe product fractions were concentrated

출처 및 근거

ORD 기록
ord-0b02c66b78d14c25967218461506b397
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781454B2

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