Triethylamine → HCID 66745168, compound

HRID 1959390Notes

Reaction equation

HRID 1959390 reaction equation
[NH:1]1[CH2:6][CH:5]=[C:4]([C:7]2[N:8]=[C:9]([C:14]3[N:22]=[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][N:16]4[N:15]=3)[C:10]([NH2:13])=[N:11][CH:12]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:30]([S:32](Cl)(=[O:34])=[O:33])[CH3:31]>C(Cl)Cl>[N:22]1[C:14]([C:9]2[C:10]([NH2:13])=[N:11][CH:12]=[C:7]([C:4]3[CH2:3][CH2:2][N:1]([S:32]([CH2:30][CH3:31])(=[O:34])=[O:33])[CH2:6][CH:5]=3)[N:8]=2)=[N:15][N:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11667Ethanesulfonyl chloride2×HCID 66744588HCID 66744588, compound

Product 1

HCID 66745168HCID 66745168, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-(1,2,3,6-tetrahydropyridin-4-yl)-3-([1,2,4]triazolo[1,5-a]pyridin-2-yl)pyrazin-2-amine (82 mg, 0.1291 mmol) was dissolved in DCM (4 mL) and treated with triethylamine (78.38 mg, 108.0 μL, 0.7746 mmol) followed by ethanesulfonyl chloride (18.26 mg, 13.46 μL, 0.1420 mmol). The reaction mixture was allowed to stir at ambient temperature for 1 hour when analysis showed SM remaining. The mixture was treated with further ethanesulfonyl chloride (16.60 mg, 12.23 μL, 0.1291 mmol) and stirred for a further hour. The reaction was diluted with DCM, washed with water and the aqueous layer extracted further with dichloromethane (2×). The combined organics were washed with saturated aqueous NaHCO3, dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by column chromatography (ISCO Companion™, 12 g column, 0-2.5% MeOH/DCM) to afford the title compound which was freeze-dried to give a yellow solid (9 mg, 17% Yield). 1H NMR (400.0 MHz, DMSO) d 1.24 (t, J=7.4 Hz, 3H), 2.71 (br s, 2H), 3.14 (q, J=7.3 Hz, 2H), 3.48 (t, J=5.7 Hz, 2H), 3.98 (d, J=2.9 Hz, 2H), 6.62 (br s, 1H), 7.30-7.33 (m, 1H), 7.72 (br s, 2H), 7.75-7.79 (m, 1H), 7.98 (d, J=8.8 Hz, 1H), 8.40 (s, 1H) and 9.11 (d, J=6.7 Hz, 1H) ppm; MS (ES+) 386.0

Workup

  1. stirringstirred for a further hour
  2. washwashed with water
  3. extractionthe aqueous layer extracted further with dichloromethane (2×)
  4. washThe combined organics were washed with saturated aqueous NaHCO3
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by column chromatography (ISCO Companion™, 12 g column, 0-2.5% MeOH/DCM)

Sources & evidence

ORD record
ord-2bae4455c3214e86a396c4c29cf0c283
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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