Water → HCID 44133052, compound

HRID 1916276Notes

Reaction equation

CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][CH:16]=[C:17]([CH2:19][OH:20])[N:18]=2)=[CH:10][CH:9]=1.[OH:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[C:40]3[C:39](=[O:41])[NH:38][CH:37]=[CH:36][C:35]=3[N:34]=[C:33](SC)[C:32]=2[C:44]#[N:45])=[CH:27][CH:26]=1.O>CN(C=O)C>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[S:15][CH:16]=[C:17]([CH2:19][O:20][C:33]3[C:32]([C:44]#[N:45])=[C:31]([C:28]4[CH:29]=[CH:30][C:25]([O:24][CH2:23][CH2:22][OH:21])=[CH:26][CH:27]=4)[C:40]4[C:39](=[O:41])[NH:38][CH:37]=[CH:36][C:35]=4[N:34]=3)[N:18]=2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

64 mg (0.57 mmol) of potassium tert-butoxide were suspended in 3.5 ml of DMF, 96 mg (0.42 mmol) of [2-(4-chlorophenyl)-1,3-thiazol-4-yl]methanol [Simiti, I. et al. Arch. Pharm. 1972, 305, 509-515] and then 100 mg (0.28 mmol) of the compound from Example 21A were added and the mixture was stirred at 60° C. for 16 h. Another 64 mg (0.57 mmol) of potassium tert-butoxide were added, and the reaction was stirred once more at 80° C. overnight. Water was added, and the reaction solution was extracted 3 times with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered off and concentrated on a rotary evaporator, The crude product was and purified by preparative HPLC (Chromasil, water/acetonitrile).

Workup

stirringthe reaction was stirred once more at 80° C. overnight
extractionthe reaction solution was extracted 3 times with ethyl acetate
dry with materialThe organic phase was dried over magnesium sulfate
filtrationfiltered off
concentrationconcentrated on a rotary evaporator
custompurified by preparative HPLC (Chromasil, water/acetonitrile)

Sources & evidence

ORD record: ord-3584b186ca3b436ea2ea50f8622d84f9
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618119B2

Reaction notes

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