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

HRID 55774

반응식

HRID 55774 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-178a4d8d02b44517a92616801e71d0ec
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09433614B2

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