Pyridine → 4-isopropyl-6-(4-(1-methyl-1H-indol-5-yl)-5-(quinolin-6-ylamino)-4H-1,2,4-triazol-3-yl)benzene-1,3-diol

HRID 555953Notes

Reaction equation

[CH:1]([C:4]1[C:5]([O:38]C)=[CH:6][C:7]([O:36]C)=[C:8]([C:10]2[N:11]([C:26]3[CH:27]=[C:28]4[C:32](=[CH:33][CH:34]=3)[N:31]([CH3:35])[CH:30]=[CH:29]4)[C:12]([NH:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[CH:19]4)=[N:13][N:14]=2)[CH:9]=1)([CH3:3])[CH3:2].N1C=CC=CC=1>C(OCC)(=O)C>[CH:1]([C:4]1[CH:9]=[C:8]([C:10]2[N:11]([C:26]3[CH:27]=[C:28]4[C:32](=[CH:33][CH:34]=3)[N:31]([CH3:35])[CH:30]=[CH:29]4)[C:12]([NH:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[N:22]=[CH:21][CH:20]=[CH:19]4)=[N:13][N:14]=2)[C:7]([OH:36])=[CH:6][C:5]=1[OH:38])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 21 °C

Procedure

A tube was charged with N-(5-(5-isopropyl-2,4-dimethoxyphenyl)-4-(1-methyl-1H-indol-5-yl)-4H-1,2,4-triazol-3-yl)quinolin-6-amine (114 mg) and pyridine*HCl (4 g.), and placed under a nitrogen atmosphere. It was heated to 21° C. for 50 minutes, and then cooled. The solid was dissolved in ethyl acetate (20 mL) and washed with a saturated solution of ammonium chloride (3×20 mL). The organic layer was dried and evaporated to give 4-isopropyl-6-(4-(1-methyl-1H-indol-5-yl)-5-(quinolin-6-ylamino)-4H-1,2,4-triazol-3-yl)benzene-1,3-diol (42 mg). In some cases column chromatography was necessary for purification. 1H-NMR (CDCl3): 8.69 (dd, 1H); 8.50 (d, 1H), 8.22 (d, 1H), 7.98 (d, 1H), 7.75 (d, 1H), 7.63 (d, 1H), 7.45-7.36 (m, 2H), 7.33 (d, 1H), 7.27 (dd, 1H), 6.64 (d, 1H), 6.42 (s, 1H), 6.30 (s, 1H), 3.98 (s, 3H); 2.83 (q, 1H); 0.50 (m, 6H). MS: expected ion=491.4; observed ion=491.

Workup

temperaturecooled
washwashed with a saturated solution of ammonium chloride (3×20 mL)
customThe organic layer was dried
customevaporated

Sources & evidence

ORD record: ord-8b3e11a235c84b1f937cc455080afb4f
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053456B2

Reaction notes

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