Triethylamine → HCID 66745801, compound

HRID 1959352Notes

Reaction equation

HRID 1959352 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]3[C:11]([NH2:22])=[N:12][CH:13]=[C:14]([C:16]4[CH2:17][CH2:18][NH:19][CH2:20][CH:21]=4)[N:15]=3)[NH:7][C:6]=2[CH:23]=1.C(N(CC)CC)C.[CH3:31][N:32]([CH3:37])[S:33](Cl)(=[O:35])=[O:34]>CS(C)=O>[NH2:22][C:11]1[N:12]=[CH:13][C:14]([C:16]2[CH2:17][CH2:18][N:19]([S:33]([N:32]([CH3:37])[CH3:31])(=[O:35])=[O:34])[CH2:20][CH:21]=2)=[N:15][C:10]=1[C:8]1[NH:7][C:6]2[CH:23]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=2[N:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 66744547HCID 66744547, compound

Product 1

HCID 66745801HCID 66745801, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 3-(6-methyl-1H-benzimidazol-2-yl)-5-(1,2,3,6-tetrahydropyridin-4-yl)pyrazin-2-amine (58 mg, 0.1893 mmol) and triethylamine (38.31 mg, 52.77 μL, 0.3786 mmol) in DMSO (1.450 mL) was treated with N,N-dimethylsulfamoyl chloride (35.34 mg, 26.43 μL, 0.2461 mmol). The solution was stirred at RT for 16 hours and then partitioned between EtOAc and water. The aqueous layer was separated, organics dried over MgSO4 and concentrated in vacuo to give a yellow solid which was washed with MeOH and filtered to give the desired product (47 mg, 57% Yield). 1H NMR (400.0 MHz, DMSO) d 2.46 (s, 3H), 2.77 (s, 2H), 2.80 (s, 6H), 3.48 (s, 2H), 3.96 (d, J=3.0 Hz, 2H), 6.76 (s, 1H), 7.10 (s, 1H), 7.61-7.40 (m, 3H) and 8.34 (s, 1H) ppm; MS (ES+) 414

Workup

  1. custompartitioned between EtOAc and water
  2. customThe aqueous layer was separated
  3. dry with materialorganics dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto give a yellow solid which
  6. washwas washed with MeOH
  7. filtrationfiltered

Sources & evidence

ORD record
ord-242ae77c1ef341ca829d385f10f365aa
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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