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Ethanesulfonyl chloride → 3-(1H-benzo[d]imidazol-2-yl)-5-(1-(ethylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine

HRID 1959355
ノート
印刷プレビュー

反応式

HRID 1959355 の反応式
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]1[C:17]([NH2:28])=[N:18][CH:19]=[C:20]([C:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=2)[N:21]=1.CCN(C(C)C)C(C)C>CN(C)C=O>[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[C:16]1[C:17]([NH2:28])=[N:18][CH:19]=[C:20]([C:22]2[CH2:23][CH2:24][N:25]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH2:26][CH:27]=2)[N:21]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11667Ethanesulfonyl chloride2 回HCID 81531DiisopropylethylamineHCID 667451703-(1H-benzo[d]imidazol-2-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine

生成物 1

HCID 667445103-(1H-benzo[d]imidazol-2-yl)-5-(1-(ethylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine収率 57%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

Ethanesulfonyl chloride (16.30 mg, 12.01 μL, 0.1268 mmol) was added to a solution of 3-(1H-benzimidazol-2-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine (60 mg, 0.1153 mmol) and DIPEA (44.71 mg, 60.26 μL, 0.3459 mmol) in N,N-dimethylformamide (1 mL) and the resulting solution stirred at ambient temperature. Analysis after 30 minutes showed SM still remaining therefore the reaction was treated with further ethanesulfonyl chloride (4 μL, 0.04222 mmol). The mixture was allowed to stir for a further 10 minutes and then partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (2×), DCM (2×), dried (MgSO4), filtered and concentrated. The mixture was triturated with DCM and the resultant yellow solid dried under vacuum at 50° C. (44.33 mg, 57% Yield).

後処理

  1. stirringto stir for a further 10 minutes
  2. custompartitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc (2×), DCM (2×)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe mixture was triturated with DCM
  8. customthe resultant yellow solid dried under vacuum at 50° C. (44.33 mg, 57% Yield)

出典と根拠

ORDレコード
ord-df903866fd3b4338bf3b2238922575f9
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08410112B2

反応ノート

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