1,4-Dioxane hydrochloride → HCID 71164902, compound

HRID 2173095Notes

Reaction equation

HRID 2173095 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]([CH3:27])[CH:23]=2)[C:19]2[C:28](=[O:38])[N:29](C(OC(C)(C)C)=O)[CH2:30][C:18]=2[C:17]=1[F:39])=O)(C)(C)C.Cl.O1CCOCC1>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]([CH3:27])[CH:23]=2)[C:19]2[C:28](=[O:38])[NH:29][CH2:30][C:18]=2[C:17]=1[F:39]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 71164898HCID 71164898, compound

Product 1

HCID 71164902HCID 71164902, compound

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)-7-fluoro-4-(3-methylisothiazol-5-yl)-3-oxo-1H-pyrrolo[3,4-c]pyridine-2(3H)-carboxylate (82 mg, 0.146 mmol) in MeOH (2.0 mL) was added 4N HCl/dioxane (2.0 mL, 8.00 mmol). The reaction mixture was heated to 60° C. for 1 hour. Following reaction, the mixture was concentrated in vacuo. The residue was triturated with EtOAc and filtered. The filter cake was washed with EtOAc to yield crude desired compound as a yellow solid. The crude product was recrystallized from MeOH-Et2O to give a hydrochloride salt of the title compound as a white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.37-1.56 (m, 2H), 1.58-1.83 (m, 4H), 1.84-2.04 (m, 2H), 2.46 (s, 3H), 3.73 (br. s., 1H), 4.17-4.29 (m, 1H), 4.47 (s, 2H), 7.17 (d, J=5.37 Hz, 1H), 7.84 (br. s., 3H), 8.66 (s, 1H), 8.76 (s, 1H). ESI-MS m/z [M+H]+ calc'd for C17H20FN5OS, 362. found, 362.

Workup

  1. customreaction
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was triturated with EtOAc
  4. filtrationfiltered
  5. washThe filter cake was washed with EtOAc
  6. customto yield crude desired compound as a yellow solid
  7. customThe crude product was recrystallized from MeOH-Et2O

Sources & evidence

ORD record
ord-fda883dacc854304af71546af4c46983
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

Loading…