Methyl 6-aminonicotinate → HCID 22600033, compound

HRID 1759785Notes

Reaction equation

[CH2:1]([N:6]([C:10]1[CH:19]=[CH:18][C:17]2[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]([CH3:23])([CH3:22])[C:12]=2[CH:11]=1)[C:7](Cl)=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5].[NH2:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][N:26]=1>N1C=CC=CC=1>[CH2:1]([N:6]([C:10]1[CH:19]=[CH:18][C:17]2[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]([CH3:23])([CH3:22])[C:12]=2[CH:11]=1)[C:7](=[O:8])[NH:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][N:26]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of pentyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-carbamoyl chloride (53) (0.24 g, 0.73 mmole) in 3 mL pyridine was treated with 0.22 g of methyl 6-aminonicotinate (Bionet) and stirred at 40° C. for three days. Volatile materials were removed in vacuo and the residue was subjected to flash chromatography (SiO2, 10%-50% ethyl acetate/hexanes) to yield 37 mg of methyl 6-[3-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-nicotinate (55).

Workup

customVolatile materials were removed in vacuo

Sources & evidence

ORD record: ord-3daaf0f7f06b48f6847143704609a736
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06838472B2

Reaction notes

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