HCID 3344586, compound → HCID 44206774, compound

HRID 2401949Notes

Reaction equation

HRID 2401949 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13](Cl)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[F:16][C:17]([F:32])([F:31])[C:18]1[CH:23]=[C:22]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[CH:21]=[CH:20][N:19]=1>N1C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([N:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)[C:22]4[CH:21]=[CH:20][N:19]=[C:18]([C:17]([F:32])([F:16])[F:31])[CH:23]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 3344586HCID 3344586, compoundHCID 591291541-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride

Product 1

HCID 44206774HCID 44206774, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
115 °C

Procedure

To 1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride (45 mg, 0.2 mmol) in pyridine (2 mL) was added N-(2-(trifluoromethyl)pyridin-4-yl)pyridin-2-amine (48 mg, 0.2 mmol) and the reaction mixture was stirred at 115° C. for 15 hours. The solvent was evaporated to dryness and the residue redissolved in DMF, filtered and purified by reverse-phase preparative liquid chromatography utilizing a gradient of 0-99% acetonitrile in water containing 0.05% trifluoracetic acid to yield the pure product. ESI-MS m/z calc. 427.4, found 428.1 (M+1)+. Retention time 2.91 minutes.

Workup

  1. customThe solvent was evaporated to dryness
  2. dissolutionthe residue redissolved in DMF
  3. filtrationfiltered
  4. custompurified by reverse-phase preparative liquid chromatography
  5. customto yield the pure product

Sources & evidence

ORD record
ord-04bec7058dc440bc905f99eb884e1111
Source dataset
uspto-grants-2014_08
Patent number
US08796312B2

Reaction notes

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