Cyclohexanemethanol → 2-[4-(3-Bromo-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acid cyclohexylmethyl ester

HRID 585149Notes

Reaction equation

[CH:1]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:9][C:10]1[CH:11]=[C:12]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[O:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([N:21]2[C:26](=[O:27])[NH:25][C:24](=[O:28])[C:23]([C:29](O)=[O:30])=[N:22]2)=[CH:16][C:15]=1[CH3:32].C(N=C=NC(C)C)(C)C>CN(C=O)C.CN(C)C1C=CN=CC=1>[CH:1]1([CH2:7][O:8][C:29]([C:23]2[C:24](=[O:28])[NH:25][C:26](=[O:27])[N:21]([C:17]3[CH:18]=[C:19]([CH3:20])[C:14]([O:13][C:12]4[CH:33]=[CH:34][C:35]([O:36][CH3:37])=[C:10]([Br:9])[CH:11]=4)=[C:15]([CH3:32])[CH:16]=3)[N:22]=2)=[O:30])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of cyclohexylmethanol (9 μmol) in DMF were added sequentially solutions of 2-[4-(3-bromo-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acid (5 μmol), diisopropylcarbodiimide (10 mmol) and 4-dimethylaminopyridine (10 μmol). The resulting soution was shaken at 50° C. for 18 h. HPLC and LCMS shows the starting material to be consumed and the desired product present. MS Calc.: 557.1; Found: 556.1 (M−1).

Workup

customto be consumed

Sources & evidence

ORD record: ord-b3cffc801c164c65999a44147a04a8fa
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06930107B2

Reaction notes

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