Dimethylformamide → HCID 86722692, compound

HRID 1480470Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][OH:10].[C:11]([O:17][CH2:18][N:19]1[CH:23]=[C:22]([CH2:24][CH2:25][CH2:26][C:27](=[O:35])[NH:28][CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[N:21]=[N:20]1)(=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13].CN([CH:39]=[O:40])C>CCOC(C)=O>[C:11]([O:17][CH2:18][N:19]1[CH:23]=[C:22]([CH2:24][CH2:25][CH2:26][C:27]([NH:28][CH:29]2[CH2:30][CH2:31][N:32]([C:39]([O:10][CH2:9][C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])=[O:40])[CH2:33][CH2:34]2)=[O:35])[N:21]=[N:20]1)(=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of commercially available (2,4-dichlorophenyl)methanol (137 mg, 0.774 mmol) in DMF (2 mL) at RT was added CU (125 mg, 0.774 mmol). The reaction mixture was allowed to heat at 50° C. for 20 hrs. (4-(4-oxo-4-(piperidin-4-ylamino)butyl)-1H-1,2,3-triazol-1-yl)methyl pivalate (Example 37, step 5)(272 mg, 0.774 mmol) was added and the reaction mixture was stirred at 50° C. for 10 hrs. The reaction mixture was diluted with EtOAc and washed with a saturated solution of sodium bicarbonate and brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification was carried out by chromatography on silica eluting with 0-100% EtOAc in iso-hexane to afford the title product;

Workup

washwashed with a saturated solution of sodium bicarbonate and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customPurification

Sources & evidence

ORD record: ord-76a2d418de294e48aa58978743cbaa2d
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409895B2

Reaction notes

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