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5-Chloro-2-methoxybenzoyl chloride → HCID 178490645, compound

HRID 717247
Notes
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Reaction equation

HRID 717247 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][N:8]([CH2:11][C@H:12]2[CH2:16][CH2:15][CH2:14][O:13]2)[C:7](=[NH:17])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([O:28][CH3:29])=[C:23]([CH:27]=1)[C:24](Cl)=[O:25]>O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][N:8]([CH2:11][C@H:12]2[CH2:16][CH2:15][CH2:14][O:13]2)/[C:7](=[N:17]/[C:24](=[O:25])[C:23]2[CH:27]=[C:19]([Cl:18])[CH:20]=[CH:21][C:22]=2[O:28][CH3:29])/[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 123841765-Chloro-2-methoxybenzoyl chlorideHCID 67545787(R)-4-tert-butyl-1-((tetrahydrofuran-2-yl)methyl)pyridin-2(1H)-imine

Product 1

HCID 178490645HCID 178490645, compoundYield 8.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the crude product of Example 61A (0.8 g, 1.7 mmol) in tetrahydrofuran (10 mL) were added 5-chloro-2-methoxybenzoyl chloride (0.4 g, 1.9 mmol) and triethylamime (0.7 mL, 5.1 mmol). After stirring at 60° C. for 14 h, the reaction mixture was cooled and quenched with saturated NaHCO3 (10 mL). The aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-5% methanol in dichloromethane) to provide 60 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.26 (s, 9H), 1.50-1.69 (m, 1H), 1.69-2.09 (m, 3H), 3.57-3.70 (m, 1H), 3.75 (s, 3H), 3.76-3.86 (m, 1H), 4.00 (dd, J=12.9, 8.5 Hz, 1H), 4.30 (dd, 1H), 4.57 (dd, J=12.7, 3.2 Hz, 1H), 6.87 (dd, J=7.0, 2.2 Hz, 1H), 7.03 (d, J=8.8 Hz, 1H), 7.34 (dd, J=8.8, 2.7 Hz, 1H), 7.53 (d, J=2.7 Hz, 1H), 7.95 (d, J=7.1 Hz, 1H), 8.28 (d, J=2.4 Hz, 1H) MS (ESI+) m/z 403 (M+H)+.

Workup

  1. temperaturethe reaction mixture was cooled
  2. customquenched with saturated NaHCO3 (10 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×20 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-555899b783e14487bf4e5fe999d26be5
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09193713B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes