Anthranilic Acid → HCID 11618024, compound

HRID 2422654Notes

Reaction equation

[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH3:11][NH2:12].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.OC1[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]1.[C:37]1(=O)[CH2:40][CH2:39][CH2:38]1>>[CH3:11][N:12]1[C:1](=[O:10])[C:2]2[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:4]=[C:19]1[C:18]1[CH:21]=[CH:22][C:15]([O:14][CH:13]2[CH2:29][CH2:28][N:27]([CH:37]3[CH2:40][CH2:39][CH2:38]3)[CH2:26][CH2:25]2)=[CH:16][CH:17]=1

Participants

Reactant 5

HCID 227Anthranilic Acid

HCID 6329Methylamine

HCID 14496Cyclobutanone

HCID 312444-Methoxybenzaldehyde

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 11618024HCID 11618024, compound

Procedure

The entitled compound was obtained according to the method of Example 85 but using anthranilic acid, methylamine, 4-methoxybenzaldehyde, tert-butyl 4-hydroxytetrahydro-1(2H)-pyridinecarboxylate, and cyclobutanone. The obtained compound was further purified through reversed-phase high-performance liquid chromatography (acetonitrile-water) to give a colorless solid (m.p. 167.8-171.2° C.).

Workup

customThe entitled compound was obtained
customThe obtained compound was further purified through reversed-phase high-performance liquid chromatography (acetonitrile-water)

Sources & evidence

ORD record: ord-1a8efbf46c5841a7a115d78b190adbb7
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960394B2

Reaction notes

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