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Pyridine → 2-[4-Fluoro-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)benzamide

HRID 644169
Notes
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Reaction equation

HRID 644169 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:16]=2[C:17]([OH:19])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.C(Cl)(=O)C(Cl)=O.[Cl:37][C:38]1[CH:39]=[CH:40][C:41]([NH:44][C:45](=[O:53])[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[NH2:52])=[N:42][CH:43]=1>C(Cl)Cl.CN(C=O)C>[F:24][C:22]1[CH:21]=[CH:20][C:16]([C:17]([NH:52][C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=2[C:45]([NH:44][C:41]2[CH:40]=[CH:39][C:38]([Cl:37])=[CH:43][N:42]=2)=[O:53])=[O:19])=[C:15]([O:14][CH:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:9][CH2:10]2)[CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1049Pyridine2×HCID 65578Oxalyl chlorideHCID 219063812-amino-N-(5-chloropyridin-2-yl)benzamideHCID 576024392-(1-tert-Butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoic acid

Product 1

HCID 685302072-[4-Fluoro-2-(1-tert-butoxycarbonylpiperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)benzamideYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

The 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoic acid (507 mg, 2.05 mmol) was diluted with methylene chloride (20 mL). DMF (4 drops) and pyridine (0.2 mL, 2.47 mmol) were added, followed by oxalyl chloride (0.2 mL, 2.29 mmol). Vigorous bubbling occurred. After 1.5 hours, the reaction was concentrated in vacuo. The residue was diluted with methylene chloride (20 mL). N-(5-Chloropyridin-2-yl)-2-aminobenzamide (507 mg, 2.05 mmol) was added, followed by pyridine (0.2 mL, 2.47 mmol). After stirring overnight, the reaction was diluted with methylene chloride (100 mL) and washed with water (2×10 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated. The crude residue was purified by flash column chromatography (100% CH2Cl2 to 10% EtOAc/CH2Cl2) to give the desired product (992 mg, 1.74 mmol, 85%) as a white solid.

Workup

  1. customVigorous bubbling
  2. concentrationthe reaction was concentrated in vacuo
  3. additionThe residue was diluted with methylene chloride (20 mL)
  4. washwashed with water (2×10 mL)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by flash column chromatography (100% CH2Cl2 to 10% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-43bc4ad42ba94d33bcc9e35c0d537f6e
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07700628B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes