HCID 59451573, compound → HCID 59451503, compound

HRID 1875031Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[C:16]([NH:21][C:22](=[O:30])[CH2:23][CH2:24][O:25]C(C)(C)C)[CH:15]=3)=[O:11])=[C:4]([F:31])[C:3]=1[O:32][C:33]1[CH:38]=[C:37]([C:39]#[N:40])[CH:36]=[C:35]([Cl:41])[CH:34]=1>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[C:16]([NH:21][C:22](=[O:30])[CH2:23][CH2:24][OH:25])[CH:15]=3)=[O:11])=[C:4]([F:31])[C:3]=1[O:32][C:33]1[CH:38]=[C:37]([C:39]#[N:40])[CH:36]=[C:35]([Cl:41])[CH:34]=1

Participants

Conditions

Temperature: 105 °C

Procedure

N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-6-({3-[(1,1-dimethylethyl)oxy]propanoyl}amino)-1H-indole-2-carboxamide (0.049 g, 0.082 mmol) was dissolved in 4N HCl in dioxane (3 mL). The mixture was heated in a 105° C. oil bath under a reflux condenser for 3 days. The solvent was evaporated and the residue was purified by reverse phase HPLC (acetonitrile:water with 0.1% TFA) to give the title compound (0.009 g, 20%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.48 (br. s., 1H), 9.82 (s, 1H), 8.69-9.06 (m, 1H), 7.91-7.99 (m, 1H), 7.78 (s, 1H), 7.42-7.56 (m, 4H), 7.35 (t, 1H), 7.08 (d, 2H), 4.30-4.70 (m, 2H), 3.54-3.82 (m, 2H), 2.39-2.46 (m, 2H). ES MS: m/z 541 (M+1).

Workup

customThe solvent was evaporated
customthe residue was purified by reverse phase HPLC (acetonitrile:water with 0.1% TFA)

Sources & evidence

ORD record: ord-d25d3a8a26294dca904091249614961a
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304419B2

Reaction notes

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