Hydrochloric Acid → HCID 67318311, compound

HRID 132236Notes

Reaction equation

HRID 132236 reaction equation
[F:1][C:2]1[N:7]=[C:6]([NH:8]C(=O)C(C)(C)C)[C:5]([CH:15](O)[CH:16]([CH:21]2[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]2)[C:17](OC)=[O:18])=[CH:4][CH:3]=1.[ClH:35]>CO.O>[ClH:35].[F:1][C:2]1[N:7]=[C:6]2[C:5]([CH:15]=[C:16]([CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[C:17](=[O:18])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59731933HCID 59731933, compound

Product 1

HCID 67318311HCID 67318311, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The mixture of tert-butyl 4-(1-(6-fluoro-2-pivalamidopyridin-3-yl)-1-hydroxy-3-methoxy-3-oxopropan-2-yl)piperidine-1-carboxylate (238 mg, 0.494 mmol), and concentrated HCl (1 mL) in MeOH (1 mL) and H2O (1 mL) was refluxed under N2 over night. The solvents were removed on rotary vacuum, the residue, as a yellow solid, was triturated with cold EtOH (2×3 mL), filtrated and dried under vacuum to afford an expected product, a yellow solid (139 mg, 99% yield); 1H NMR (400 MHz, MeOD) δ ppm 1.27 (s, 1 H), 1.83-1.95 (m, 2 H), 2.13 (d, J=14.10 Hz, 2 H), 3.06-3.18 (m, 3 H), 3.49 (d, J=12.84 Hz, 2 H), 6.47 (d, J=8.81 Hz, 1 H), 7.69 (s, 1 H), 7.85 (d, J=9.06 Hz, 1 H); Mass spec. 248.13 (MH+), Calc. for C13H14FN3O 247.11

Workup

  1. temperaturewas refluxed under N2 over night
  2. customThe solvents were removed on rotary vacuum
  3. customthe residue, as a yellow solid, was triturated with cold EtOH (2×3 mL)
  4. filtrationfiltrated
  5. customdried under vacuum

Sources & evidence

ORD record
ord-31d9c08bf6f149cd96214ae49aa7de37
Source dataset
uspto-grants-2008_06
Patent number
US07384930B2

Reaction notes

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