Ethanol → HCID 71164905, compound

HRID 2173064Notes

Reaction equation

HRID 2173064 reaction equation
C(OC([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[N:21]=[C:20]([C:22]2[S:26][N:25]=[C:24]([CH2:27][CH3:28])[CH:23]=2)[C:19]2[C:29](=[O:39])[N:30](C(OC(C)(C)C)=O)[CH2:31][C:18]=2[C:17]=1[F:40])=O)(C)(C)C.Cl.O1CCOCC1.CCO>CO>[NH2:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[N:21]=[C:20]([C:22]2[S:26][N:25]=[C:24]([CH2:27][CH3:28])[CH:23]=2)[C:19]2[C:29](=[O:39])[NH:30][CH2:31][C:18]=2[C:17]=1[F:40]

Participants

5

Reactant 3

HCID 702EthanolHCID 204431481,4-Dioxane hydrochlorideHCID 71164885HCID 71164885, compound

Product 1

HCID 71164905HCID 71164905, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of tert-butyl 6-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-(3-ethylisothiazol-5-yl)-7-fluoro-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (80 mg, 0.139 mmol) in MeOH (1.0 mL) was added 4N HCl/dioxane (1.0 mL, 4.00 mmol). The mixture was heated to 60° C. for 1 h and was subsequently concentrated in vacuo. The residue was triturated with EtOAc and filtered. The filter cake was washed with EtOAc to give a yellow solid, which was suspended into EtOH. The mixture was stirred at 80° C. for 30 minutes and then cooled to room temperature. The resulting precipitate was collected by filtration and washed with EtOH to give a hydrochloride salt of the title compound as an off-white solid (20.6 mg, 36%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.26 (t, J=7.57 Hz, 3H), 1.39-1.55 (m, 2H), 1.56-1.83 (m, 4H), 1.83-2.04 (m, 2H), 2.81 (q, J=7.65 Hz, 2H), 3.77 (br s, 1H), 4.18-4.30 (m, 1H), 4.41-4.53 (m, 2H), 7.16 (d, J=5.86 Hz, 1H), 7.82 (br s, 3H), 8.66 (s, 1H), 8.80 (s, 1H). ESI-MS m/z [M+H]+ calc'd for C18H22FN5OS, 376. found, 376.

Workup

  1. concentrationwas subsequently concentrated in vacuo
  2. customThe residue was triturated with EtOAc
  3. filtrationfiltered
  4. washThe filter cake was washed with EtOAc
  5. customto give a yellow solid, which
  6. temperaturecooled to room temperature
  7. filtrationThe resulting precipitate was collected by filtration
  8. washwashed with EtOH

Sources & evidence

ORD record
ord-17b55cb1d873423c8c6a7a49c8e8bb5f
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

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