Hydrochloric Acid → HCID 58464922, compound

HRID 1185394Notes

Reaction equation

HRID 1185394 reaction equation
Cl.[F:2][C:3]1([F:47])[CH:9]([NH:10]C(=O)C(F)(F)F)[CH2:8][CH2:7][N:6]([C:17]2[N:21]([CH3:22])[N:20]=[CH:19][C:18]=2[NH:23][C:24]([C:26]2[N:27]=[C:28]([C:39]3[C:44]([F:45])=[CH:43][CH:42]=[CH:41][C:40]=3[F:46])[S:29][C:30]=2[NH:31]C(=O)OC(C)(C)C)=[O:25])[CH2:5][CH2:4]1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CO>[NH2:31][C:30]1[S:29][C:28]([C:39]2[C:40]([F:46])=[CH:41][CH:42]=[CH:43][C:44]=2[F:45])=[N:27][C:26]=1[C:24]([NH:23][C:18]1[CH:19]=[N:20][N:21]([CH3:22])[C:17]=1[N:6]1[CH2:7][CH2:8][CH:9]([NH2:10])[C:3]([F:2])([F:47])[CH2:4][CH2:5]1)=[O:25]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 87401043HCID 87401043, compound

Product 1

HCID 58464922HCID 58464922, compoundYield 27.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

HCl in 1,4-dioxane (4 M, 2 mL) was added to a solution of Example 55 (20 mg, 0.03 mmol) in MeOH (0.5 mL). This mixture was stirred at room temperature for 18 hr. The solvents were removed under reduced pressure and the crude product re-dissolved in MeOH/water (1:1, 5 mL). K2CO3 (0.3 g, 7, 2.2 mmol) was added and the mixture heated and stirred at 60° C. for 3 hr before being cooled to room temperature. The mixture was concentrated under reduced pressure and the residue purified by preparative HPLC to yield 351 as a white solid (4 mg, 25%). 1H NMR (400 MHz, CDCl3) δ 9.02 (s, 1H), 7.88 (s, 1H), 7.37-7.28 (m, 1H), 7.08-6.98 (m, 2H), 6.15 (s, 2H), 3.73 (s, 3H), 3.39-3.13 (m, 6H), 2.46-2.34 (m, 1H), 2.22-2.03 (m, 2H), 1.99-1.89 (m, 1H), 1.83-1.78 (m, 1H). LCMS (ES+) m/z 484.0 (M+1).

Workup

  1. customThe solvents were removed under reduced pressure
  2. dissolutionthe crude product re-dissolved in MeOH/water (1:1, 5 mL)
  3. temperaturethe mixture heated
  4. stirringstirred at 60° C. for 3 hr
  5. temperaturebefore being cooled to room temperature
  6. concentrationThe mixture was concentrated under reduced pressure
  7. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-59eac31ee9c44480913a18a8b6f6f42d
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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