1,2-Dichloroethane → 4-Amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-3-iodobenzamide

HRID 2281181ノート

反応式

HRID 2281181 の反応式
Cl.Cl.[NH2:3][CH:4]1[CH:9]2[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]2)[CH2:5]1.[NH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][C:14]=1[I:22].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[NH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH:3][CH:4]2[CH:9]3[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]3)[CH2:5]2)=[O:18])=[CH:15][C:14]=1[I:22]

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 164614-Amino-3-iodobenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 197853Quinuclidine, 3-amino-, dihydrochloride

生成物 1

HCID 589329434-Amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-3-iodobenzamide収率 90.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 2.04 g (10.3 mmol) of 3-aminoquinuclidine dihydrochloride, 2.70 g (10.3 mmol) of 4-amino-3-iodobenzoic acid, 1.39 g (10.3 mmol) of HOBt, 2.16 g (11.3 mmol) of EDC and 6.63 g (51.3 mmol) of N,N-diisopropylethylamine in 150 ml of DMF was stirred at room temperature for 16 h. 300 ml of water were added, and the aqueous phase was extracted three times with 300 ml of ethyl acetate each time. The combined organic phases were dried over sodium sulfate and the solvent was distilled off in vacuo. The residue was purified on a flash column (mobile phase: dichloromethane/methanol/triethylamine 90:10:0.2). 3.45 g (87%) of the desired title compound were obtained.

後処理

  1. extractionthe aqueous phase was extracted three times with 300 ml of ethyl acetate each time
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. distillationthe solvent was distilled off in vacuo
  4. customThe residue was purified on a flash column (mobile phase: dichloromethane/methanol/triethylamine 90:10:0.2)

出典と根拠

ORDレコード
ord-bd76d74d0f2c406d8dcb04710c28358c
出典データセット
uspto-grants-2015_09
特許番号
US09139579B2

反応ノート

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