1,2-Dichloroethane → HCID 178522426、化合物

HRID 1012094ノート

反応式

HRID 1012094 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 178522426HCID 178522426、化合物収率 25.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4e1e6bfbe74e4ce9a9f3bac4b83db5b9
出典データセット
uspto-grants-2011_07
特許番号
US07977477B2

反応ノート

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