Hydroxyamine hydrochloride → HCID 172983753, compound

HRID 571365Notes

Reaction equation

HRID 571365 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C@@H:8]1[CH2:17][C@H:11]2[CH2:12][N:13]([C:15]#[N:16])[CH2:14][C@@:10]2([C:18]([N:20]2[CH2:29][CH2:28][C:27]3[N:26]=[CH:25][C:24]([C:30]([F:33])([F:32])[F:31])=[CH:23][C:22]=3[CH2:21]2)=[O:19])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:36][OH:37]>C(O)C>[C:1]([O:5][C:6](=[O:34])[NH:7][C@@H:8]1[CH2:17][C@H:11]2[CH2:12][N:13](/[C:15](=[N:36]/[OH:37])/[NH2:16])[CH2:14][C@@:10]2([C:18]([N:20]2[CH2:29][CH2:28][C:27]3[N:26]=[CH:25][C:24]([C:30]([F:32])([F:33])[F:31])=[CH:23][C:22]=3[CH2:21]2)=[O:19])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 131732812HCID 131732812, compound

Product 1

HCID 172983753HCID 172983753, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the product of Step A of Example 2 (0.12 g, 0.25 mmol), hydroxylamine hydrochloride (43.48 mg, 0.626 mmol) and TEA (0.087 mL, 0.626 mmol) in ethanol (1.2 mL) in a sealed tube in Ar was heated at 80° C. overnight. After removal of solvent, the residue was partitioned between EtOAc and brine, separated, dried over Na2SO4. Purification by CombiFlash (eluent: 8% methanol in DCM) gave the product as a white solid. 1H-NMR (400 MHz, CDCl3): δ 1.30-1.45 (m, 9H), 1.70-1.99 (m, 3H), 2.38 (br. s., 1H), 3.09 (d, J=9.3 Hz, 3H), 3.28-3.54 (m, 3H), 3.65-3.89 (m, 3H), 4.23 (d, J=5.1 Hz, 1H), 4.44-4.93 (m, 5H), 7.72 (br. s., 1H), 8.69 (s, 1H); LC/MS: C23H31F3N6O4: m/z 513 (M+H).

Workup

  1. customAfter removal of solvent
  2. customthe residue was partitioned between EtOAc and brine
  3. customseparated
  4. dry with materialdried over Na2SO4
  5. customPurification by CombiFlash (eluent: 8% methanol in DCM)

Sources & evidence

ORD record
ord-277c34a7252f4774b202bbd06c524f6d
Source dataset
uspto-grants-2015_05
Patent number
US09024017B2

Reaction notes

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