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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
Notes
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Reaction equation

HRID 1959355 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-df903866fd3b4338bf3b2238922575f9
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08410112B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes