Diisopropylethylamine → HCID 57800298, compound

HRID 913663Notes

Reaction equation

HRID 913663 reaction equation
[C:1]([C:3]1[C:4]([C:21]([F:24])([F:23])[F:22])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12]/[C:13](=[N:16]/[H])/[NH:14][OH:15])[C:7]([CH2:18][CH2:19][CH3:20])=[CH:6]2)#[N:2].[C:25]([C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30](Cl)=O)#[N:26].C(N(CC)C(C)C)(C)C>C(#N)C>[C:25]([C:27]1[CH:28]=[C:29]([C:30]2[O:15][N:14]=[C:13]([CH2:12][N:8]3[C:9]4[C:5](=[C:4]([C:21]([F:24])([F:23])[F:22])[C:3]([C:1]#[N:2])=[CH:11][CH:10]=4)[CH:6]=[C:7]3[CH2:18][CH2:19][CH3:20])[N:16]=2)[CH:33]=[CH:34][CH:35]=1)#[N:26]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3084833-Cyanobenzoyl chlorideHCID 178506477HCID 178506477, compound

Product 1

HCID 57800298HCID 57800298, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of (1Z)-2-[5-cyano-2-propyl-4-(trifluoromethyl)-1H-indol-1-yl]-N-hydroxyethanimidamide (Example 275A) (0.100 g, 0.308 mmol) in anhydrous acetonitrile (3.0 mL) under N2, was added 3-cyanobenzoyl chloride (0.204 g, 1.23 mmol) and N,N-diisopropylethylamine (0.50 mL, 5.21 mmol). The mixture was then heated in a microwave at 150° C. for 30 min. Upon cooling, the mixture was poured onto a biotage prepak column and the mixture was purified by flash chromatography (0-25% EtOAc-hexanes gradient) to give 0.079 g (59% yield) of pure product: MS (ES) m/z 435 (M+).

Workup

  1. temperatureUpon cooling
  2. additionthe mixture was poured onto a biotage prepak column
  3. customthe mixture was purified by flash chromatography (0-25% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-eda722658a85430a9d963d5c933f3a0c
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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