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Pyridine → N-(4-tert-Butylphenyl)-1-(3-(trifluoromethyl)pyridin-2-yl)-1,2,3,6-tetrahydropyridine-4-carboxamide

HRID 1246726
Notes
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Reaction equation

HRID 1246726 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[C:4]([N:9]2[CH2:14][CH:13]=[C:12]([C:15]([OH:17])=O)[CH2:11][CH2:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1.C(Cl)(C(Cl)=O)=O.N1C=CC=CC=1.[C:32]([C:36]1[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=1)([CH3:35])([CH3:34])[CH3:33]>C(Cl)Cl.C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C.O.CN(C=O)C>[C:32]([C:36]1[CH:37]=[CH:38][C:39]([NH:40][C:15]([C:12]2[CH2:11][CH2:10][N:9]([C:4]3[C:3]([C:2]([F:1])([F:19])[F:18])=[CH:8][CH:7]=[CH:6][N:5]=3)[CH2:14][CH:13]=2)=[O:17])=[CH:41][CH:42]=1)([CH3:35])([CH3:33])[CH3:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 698614-Tert-ButylanilineHCID 21904722HCID 21904722, compound

Product 1

HCID 11407011N-(4-tert-Butylphenyl)-1-(3-(trifluoromethyl)pyridin-2-yl)-1,2,3,6-tetrahydropyridine-4-carboxamideYield 534.8%

Reagents, catalysts & solvents 5

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 962WaterSolvent
HCID 1140TolueneSolvent
HCID 6228DimethylformamideSolvent
HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3′-trifluoromethyl-3,6-dihydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (60.4 mg, 0.194 mmol) and DMF (cat) in CH2Cl2 (1 mL) was added (COCl)2 (0.027 mL, 0.31 mmol). The mixture was stirred for 90 minutes, diluted with PhMe (0.5 mL), concentrated under reduced pressure to dryness, and dissolved in CH2Cl2 (1.5 mL). To the solution were added pyridine (0.027 mL, 0.33 mmol), DMAP (cat), and 4-tert-butylaniline (0.037 mL, 0.023 mmol). The mixture was stirred 1 hour, diluted with water and extracted with CH2Cl2, dried (Na2SO4), and purified by flash chromatography (7% EtOAc/CH2Cl2) to provide as a white solid (54.2 mg, 0.123 mmol, 63%): MS (ESI+) m/z 404 (M+H)+, m/z 402 (M−H)−; 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.31 (s, 9 H), 2.67 (m, 2 H), 3.53 (t, J=5.4 Hz, 2 H), 4.07 (q, J=2.9 Hz, 2 H), 6.67 (m, 1 H), 6.98 (dd, J=7.5, 4.4 Hz, 1 H), 7.36 (m, 3 H), 7.48 (m, 2 H), 7.89 (dd, J=7.8, 1.7 Hz, 1 H), 8.42 (dd, J=4.7, 1.4 Hz, 1 H).

Workup

  1. concentrationconcentrated under reduced pressure to dryness
  2. dissolutiondissolved in CH2Cl2 (1.5 mL)
  3. stirringThe mixture was stirred 1 hour
  4. extractionextracted with CH2Cl2
  5. dry with materialdried (Na2SO4)
  6. custompurified by flash chromatography (7% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-b91ab07b7cb44c69830759d677988ef6
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07129235B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes