Hydrochloric Acid → HCID 46199556, compound

HRID 1959399Notes

Reaction equation

HRID 1959399 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].C(OC([N:14]([C:22]1[C:27]([C:28]2[N:32]=[C:31]([CH3:33])[O:30][N:29]=2)=[N:26][C:25]([N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)=[CH:24][N:23]=1)C(=O)OC(C)(C)C)=O)(C)(C)C.C(N(CC)CC)C.Cl.O1CCOCC1>ClCCl>[CH2:1]([S:3]([N:37]1[CH2:38][CH2:39][N:34]([C:25]2[N:26]=[C:27]([C:28]3[N:32]=[C:31]([CH3:33])[O:30][N:29]=3)[C:22]([NH2:14])=[N:23][CH:24]=2)[CH2:35][CH2:36]1)(=[O:5])=[O:4])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 312751,4-DioxaneHCID 66744426HCID 66744426, compound

Product 1

HCID 46199556HCID 46199556, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethanesulfonyl chloride (41.38 mg, 30.49 μL, 0.3218 mmol) was added to a solution of tert-butyl N-tert-butoxycarbonyl-N-[3-(5-methyl-1,2,4-oxadiazol-3-yl)-5-piperazin-1-yl-pyrazin-2-yl]carbamate (150 mg, 0.2925 mmol) and triethylamine (59.20 mg, 81.54 μL, 0.5850 mmol) in dichloromethane (5.818 mL) at 0° C. and the resulting solution stirred at ambient temperature for 1.5 hours. The reaction was treated with HCl in dioxane (365.8 μL of 4 M, 1.463 mmol) and allowed to stir at ambient temperature overnight. The reaction was concentrated in vacuo and the resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected and freeze-dried to give the title compound (19.8 mg, 12% Yield). 1H NMR (DMSO) d 1.23 (3H, t), 2.70 (3H, s), 3.08-3.13 (2H, q), 3.31 (4H, m), 3.48 (4H, m), 6.50 (2H, br s), 8.17 (1H, s) ppm; MS (ES+) 353.99

Workup

  1. stirringto stir at ambient temperature overnight
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
  4. customThe fractions were collected
  5. customfreeze-dried

Sources & evidence

ORD record
ord-a7fed3b2216a4db980b265e1f105be6e
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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