O-(Tetrahydropyran-2-yl)hydroxylamine → HCID 87208899, compound

HRID 518213Notes

Reaction equation

HRID 518213 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][C:13]2([CH2:24][C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[C:20](/[CH:26]=[CH:27]/[C:28](O)=[O:29])[CH:21]=3)[O:16]2)[CH2:12][CH2:11]1.[NH2:31][O:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][O:34]1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][C:13]2([CH2:24][C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[C:20](/[CH:26]=[CH:27]/[C:28]([NH:31][O:32][CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][O:34]4)=[O:29])[CH:21]=3)[O:16]2)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 66932399HCID 66932399, compound

Product 1

HCID 87208899HCID 87208899, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-3-{1′-[2-(2-Fluoro-phenyl)-ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid (165 mg, 0.370 mmol) was suspended in DCM (5 ml). TEA (0.075 ml, 0.54 mmol) was added and the clear solution was treated with NH2OTHP following the procedure described in Example 1, Step B, giving (E)-3-{1′-[2-(2-fluoro-phenyl)-ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide (163 mg) as a yellow solid. The compound was then dissolved in DCM (5 ml) and treated with 4 M HCl in dioxane (0.5 ml, 2 mmol) as described in Example 55, Step D, giving the hydroxamic acid as a light yellow solid (103 mg, hydrochloride salt).

Sources & evidence

ORD record
ord-dffe09ee10814012bb782ee4194c457e
Source dataset
uspto-grants-2015_08
Patent number
US09115148B2

Reaction notes

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