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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
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HRID 1959355 반응식
[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
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참가 물질

5

반응물 3

HCID 11667Ethanesulfonyl chloride2회HCID 81531DiisopropylethylamineHCID 667451703-(1H-benzo[d]imidazol-2-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine

생성물 1

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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-df903866fd3b4338bf3b2238922575f9
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08410112B2

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