O-(Tetrahydropyran-2-yl)hydroxylamine → HCID 87208939, compound

HRID 2046750Notes

Reaction equation

HRID 2046750 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][C:14]3([CH2:25][C:24](=[O:26])[C:23]4[C:18](=[CH:19][CH:20]=[C:21](/[CH:27]=[CH:28]/[C:29](O)=[O:30])[CH:22]=4)[O:17]3)[CH2:13][CH2:12]2)[CH:6]=[CH:7][CH:8]=1.[NH2:32][O:33][CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][O:35]1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][C:14]3([CH2:25][C:24](=[O:26])[C:23]4[C:18](=[CH:19][CH:20]=[C:21](/[CH:27]=[CH:28]/[C:29]([NH:32][O:33][CH:34]5[CH2:39][CH2:38][CH2:37][CH2:36][O:35]5)=[O:30])[CH:22]=4)[O:17]3)[CH2:13][CH2:12]2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 66932519HCID 66932519, compound

Product 1

HCID 87208939HCID 87208939, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(E)-3-{1′-[2-(3-Methoxy-phenyl)-ethyl]-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid (165 mg, 0.360 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-(3-methoxy-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 a light yellow solid (103 mg, hydrochloride salt).

Sources & evidence

ORD record
ord-78db1f75823048acb5226fca072e483c
Source dataset
uspto-grants-2013_11
Patent number
US08592444B2

Reaction notes

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