Pyridine → HCID 11384023, compound

HRID 403026Notes

Reaction equation

HRID 403026 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[NH2:24][C:25]1[CH:26]=[C:27]([CH:34]=[CH:35][C:36]=1[CH3:37])[C:28]([NH:30][CH:31]1[CH2:33][CH2:32]1)=[O:29].N1C=CC=CC=1>C(Cl)Cl.CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([NH:24][C:25]2[CH:26]=[C:27]([CH:34]=[CH:35][C:36]=2[CH3:37])[C:28]([NH:30][CH:31]2[CH2:32][CH2:33]2)=[O:29])=[O:15])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 738804-(Benzyloxy)benzoic acidHCID 119838543-amino-N-cyclopropyl-4-methylbenzamide

Product 1

HCID 11384023HCID 11384023, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 4-benzyloxybenzoic acid (11.0 g, 48 mmol) in DCM (100 mL) at 0° C. was added oxalyl chloride (8.4 mL, 96 mmol) followed by DMF (two drops). The resulting mixture was stirred at room temperature for 2 hours. The mixture was evaporated giving a white solid which was dissolved in DCM (50 mL). The resulting solution was added portionwise to a stirred solution of 3-amino-N-cyclopropyl-4-methylbenzamide (7.61 g, 40 mmol) and pyridine (7.76 mL, 96 mmol) in DCM (100 mL) at 0° C. The resulting mixture was stirred at room temperature for 2 hours. The solid was collected by filtration and washed three times with DCM to give the title compound as a white solid (13.9 g, 87%); NMR Spectrum: (DMSOd6) 0.60 (m, 4H), 2.25 (s, 3H), 2.84 (m, 1H), 5.20 (s, 2H), 7.14 (d, 2H), 7.39 (m, 6H), 7.63 (d, 1H), 7.79 (s, 1H), 7.97 (d, 2H), 8.37 (s, 1H), 9.82 (s, 1H); Mass Spectrum: M+H+ 399.

Workup

  1. customThe mixture was evaporated
  2. customgiving a white solid which
  3. stirringThe resulting mixture was stirred at room temperature for 2 hours
  4. filtrationThe solid was collected by filtration
  5. washwashed three times with DCM

Sources & evidence

ORD record
ord-a73267fceef644d98dac76e30de0a36a
Source dataset
uspto-grants-2014_06
Patent number
US08742124B2

Reaction notes

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