Hydrochloric Acid → 2-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(6-bromo-1-benzothien-2-yl)acetamide hydrochloride

HRID 1896492

反応式

HRID 1896492 の反応式
[ClH:1].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([CH2:10][C:11]([O:13]C1C(F)=C(F)C(F)=C(F)C=1F)=O)[CH2:3]2.[Br:25][C:26]1[CH:35]=[CH:34][C:29]2[CH:30]=[C:31]([NH2:33])[S:32][C:28]=2[CH:27]=1.C(=O)([O-])[O-].Cl>CN(C=O)C.C(#N)C>[ClH:1].[N:2]12[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9]1)[CH:4]([CH2:10][C:11]([NH:33][C:31]1[S:32][C:28]3[CH:27]=[C:26]([Br:25])[CH:35]=[CH:34][C:29]=3[CH:30]=1)=[O:13])[CH2:3]2

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 19660Carbonate IonHCID 179798236-Bromobenzo[b]thiophen-2-amineHCID 86610796Pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride

生成物 1

HCID 179798252-(1-Azabicyclo[2.2.2]oct-3-yl)-N-(6-bromo-1-benzothien-2-yl)acetamide hydrochloride

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒

実験手順

89.2 mg (0.24 mmol) of pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride are dissolved in 1 ml of DMF, mixed with 71.2 mg (0.31 mmol) of 6-bromo-1-benzothiophene-2-amine and stirred at room temperature overnight. 1 g of MP-carbonate (polymer-bound carbonate, capacity: 2.5-3.5 mmol/g; from Argonaut Technologies, USA) is added. After 3 h, the polystyrene resin is filtered off and washed with THF. The combined filtrates are concentrated in vacuo, and the crude product is purified by preparative HPLC. The hydrochloride is prepared by mixing the product with a mixture of 1 M hydrochloric acid and acetonitrile and again concentrating. Drying under high vacuum results in 14 mg (14% of theory) of the title compound.

後処理

  1. waitAfter 3 h
  2. filtrationthe polystyrene resin is filtered off
  3. washwashed with THF
  4. concentrationThe combined filtrates are concentrated in vacuo
  5. customthe crude product is purified by preparative HPLC
  6. customThe hydrochloride is prepared
  7. additionby mixing the product
  8. concentrationagain concentrating
  9. customDrying under high vacuum

出典と根拠

ORDレコード
ord-5640154e8dad429e9127d6173e8b8aaa
出典データセット
uspto-grants-2013_08
特許番号
US08518967B2

関連ノート

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