6-Methylanthranilic acid → 2-[2-(2-{2-[2-(2-Methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-pyridin-3-yl]-5-methyl-4H-benz[d][1,3]oxazin-4-one

HRID 1360324Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][C:15]1[N:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=O.[CH3:24][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]([NH2:34])[C:30]=1[C:31](O)=[O:32]>CC#N>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][C:15]1[C:16]([C:17]2[O:19][C:31](=[O:32])[C:30]3[C:25]([CH3:24])=[CH:26][CH:27]=[CH:28][C:29]=3[N:34]=2)=[CH:20][CH:21]=[CH:22][N:23]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of compound D (164.7 mg, 0.50 mmol) in CH3CN (2.0 mL) was treated with N,N′-carbonyldiimidazole (CDI, 81.1 mg, 0.50 mmol) at 65° C. under N2 for 1 h. 6-Methylanthranilic acid (75.6 mg, 0.50 mmol) was added at 25° C., and the mixture was heated at 65° C. overnight. Additional CDI (81.1 mg, 0.50 mmol) was added and the mixture was heated at 65° C. for 8 h. The crude mixture was purified by C18 reverse phase chromatography to provide compound 52 as colorless gum (120.0 mg, 54%). 1H-NMR (400 mHz, CDCl3) δ 8.29 (dd, 1H, J=5.2 Hz, J=2.0 Hz), 8.25 (dd, 1H, J=7.6 Hz, J=2.0 Hz), 7.66 (t, 1H, J=7.8 Hz), 7.50 (d, 1H, J=7.6 Hz), 7.31 (d, 1H, J=7.6 Hz), 7.01 (dd, 1H, J=7.4 Hz, J=5.0 Hz), 4.62 (m, 2H), 3.94 (m, 2H), 3.78 (m, 2H), 3.62 (m, 8H), 3.51 (m, 2H), 3.34 (s, 3H), 2.82 (s, 3H). ESMS: 445.0 [M+H]+, 467.0 [M+Na]+.

Workup

temperaturethe mixture was heated at 65° C. for 8 h
customThe crude mixture was purified by C18 reverse phase chromatography

Sources & evidence

ORD record: ord-0b12b95360c94e70822b81f803955cb3
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879846B2

Reaction notes

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