Hydrochloric Acid → HCID 66744683, compound

HRID 1959401Notes

Reaction equation

HRID 1959401 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[S:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH:9]=[C:8]1[C:16]1[C:17]([N:28](C(OC(C)(C)C)=O)C(=O)OC(C)(C)C)=[N:18][CH:19]=[C:20]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[N:21]=1.C(N(CC)CC)C.Cl.O1CCOCC1>ClCCl>[S:7]1[C:8]([C:16]2[C:17]([NH2:28])=[N:18][CH:19]=[C:20]([N:22]3[CH2:27][CH2:26][N:25]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH2:24][CH2:23]3)[N:21]=2)=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]1=2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11667Ethanesulfonyl chlorideHCID 312751,4-DioxaneHCID 66744445HCID 66744445, compound

Product 1

HCID 66744683HCID 66744683, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethanesulfonyl chloride (25.43 mg, 18.74 μL, 0.1978 mmol) was added to a solution of tert-butyl N-[3-(benzothiophen-2-yl)-5-piperazin-1-yl-pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate (92 mg, 0.1798 mmol) and triethylamine (36.39 mg, 50.12 μL, 0.3596 mmol) in dichloromethane (3.965 mL) at 0° C. and the resulting solution stirred at room temperature for 1.5 hours. The reaction was then treated with HCl in dioxane (224.8 μL of 4 M, 0.8990 mmol) and allowed to stir at ambient temperature overnight. The mixture 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, passed through a sodium bicarbonate cartridge and freeze-dried to give the title compound as a yellow solid (14.4 mg, 20% Yield). 1H NMR (DMSO) d 1.24 (3H, t), 2.51 (2H, q), 3.30 masked signal, 3.52 (4H, m), 5.91 (2H, br s), 7.36-7.40 (2H, m), 7.84-7.86 (1H, m), 7.92 (1H, s), 7.95 (1H, m), 8.06 (1H, s) ppm; MS (ES+) 404.02

Workup

  1. stirringto stir at ambient temperature overnight
  2. concentrationThe mixture 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-614e456d398d4ce4893c7012f3bdd1da
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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