1,2-Dichloroethane → HCID 178522426, 화합물

HRID 1012094노트

반응식

HRID 1012094 반응식
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:3]=1[C:4]([NH:6][C:7]1[C:8]([C:12](O)=O)=[N:9][NH:10][CH:11]=1)=[O:5].[N:20]1([CH2:26][C:27]2[CH:28]=[C:29]([NH2:34])[C:30]([NH2:33])=[CH:31][CH:32]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:3]=1[C:4]([NH:6][C:7]1[C:8]([C:12]2[NH:33][C:30]3[CH:31]=[CH:32][C:27]([CH2:26][N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:28][C:29]=3[N:34]=2)=[N:9][NH:10][CH:11]=1)=[O:5]

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 251933094-(Morpholinomethyl)benzene-1,2-diamineHCID 178524952HCID 178524952, 화합물

생성물 1

HCID 178522426HCID 178522426, 화합물수율 25.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-(2,6-dichloro-benzoylamino)-1H-pyrazole-3-carboxylic acid (75 mg, 0.25 mmol), 4-morpholin-4-ylmethyl-benzene-1,2-diamine (52 mg, 0.25 mmol), EDC (58 mg, 0.3 mmol) and HOBt (41 mg, 0.3 mmol) in DMF (4 ml) was stirred at ambient temperature for 48 hours. The mixture was partitioned between EtOAc and saturated aqueous NaHCO3 and the organic portion washed with saturated aqueous NH4Cl, dried (MgSO4) and reduced in vacuo. The residue was taken up in AcOH and heated at 100° C. for 14 hours. cooled to ambient temperature and reduced in vacuo. The residue was purified via flash column chromatography eluting with CH2Cl2-MeOH (20:1-10:1) to give 2,6-dichloro-N-[3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide (30 mg) as a pink solid. (LC/MS: Rt 2.12, [M+H]+ 471.14).

후처리

  1. customThe mixture was partitioned between EtOAc and saturated aqueous NaHCO3
  2. washthe organic portion washed with saturated aqueous NH4Cl
  3. dry with materialdried (MgSO4)
  4. temperatureheated at 100° C. for 14 hours
  5. temperaturecooled to ambient temperature
  6. customThe residue was purified via flash column chromatography
  7. washeluting with CH2Cl2-MeOH (20:1-10:1)

출처 및 근거

ORD 기록
ord-4e1e6bfbe74e4ce9a9f3bac4b83db5b9
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977477B2

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