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1,2-Dichloroethane → N-[(3S)-1-Azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzothiophene-2-carboxamide hydrochloride

HRID 1012706
ノート
印刷プレビュー

反応式

HRID 1012706 の反応式
C(Cl)C[Cl:3].C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[Br:22][C:23]1[C:31]2[S:30][C:29]([C:32]([OH:34])=O)=[CH:28][C:27]=2[CH:26]=[CH:25][CH:24]=1.Cl.Cl.[NH2:37][C@H:38]1[CH:43]2[CH2:44][CH2:45][N:40]([CH2:41][CH2:42]2)[CH2:39]1.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[ClH:3].[N:40]12[CH2:45][CH2:44][CH:43]([CH2:42][CH2:41]1)[C@H:38]([NH:37][C:32]([C:29]1[S:30][C:31]3[C:23]([Br:22])=[CH:24][CH:25]=[CH:26][C:27]=3[CH:28]=1)=[O:34])[CH2:39]2
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 6

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 12494973(3S)-1-azabicyclo[2.2.2]octan-3-amine dihydrochlorideHCID 179795837-Bromo-1-benzothiophene-2-carboxylic acid

生成物 1

HCID 67313990
N-[(3S)-1-Azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzothiophene-2-carboxamide hydrochloride

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

3.58 g (18.7 mmol) of EDC, 2.52 g (18.7 mmol) of HOBt and 7.8 ml (56 mmol) of triethylamine are added to a solution, cooled to 0° C., of 4.0 g (15.6 mmol) of 7-bromo-1-benzothiophene-2-carboxylic acid (Example 7A) and 3.10 g (15.6 mmol) of (S)-3-aminoquinuclidine dihydrochloride in 50 ml of DMF. The mixture is stirred at room temperature for 18 h. The reaction is stopped by adding 10% strength sodium bicarbonate solution. The precipitate resulting after addition of ethyl acetate is filtered off. The aqueous phase is extracted with ethyl acetate, the combined organic phases are dried over sodium sulphate and concentrated, and the residue is dried under high vacuum. 4.70 g (68% of theory) of the title compound are obtained. The spectroscopic data agree with those of the enantiomeric compound (Example 8A).

後処理

  1. customThe precipitate resulting
  2. filtrationis filtered off
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. dry with materialthe combined organic phases are dried over sodium sulphate
  5. concentrationconcentrated
  6. customthe residue is dried under high vacuum

出典と根拠

ORDレコード
ord-8c3f6bdd27eb4d65b2cd2db08a42e94d
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07977485B2

反応ノート

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