Triethylamine → HCID 58138928, compound

HRID 2061568Notes

Reaction equation

HRID 2061568 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][N:4]=1.C(Cl)(=O)C(Cl)=O.[F:20][C:21]([F:34])([F:33])[C:22]1[NH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][C:27]([CH2:31][NH2:32])=[CH:26][CH:25]=2.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[F:34][C:21]([F:20])([F:33])[C:22]1[NH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][C:27]([CH2:31][NH:32][C:7]([C:6]1[CH:5]=[N:4][C:3]([C:2]([F:1])([F:13])[F:12])=[CH:11][CH:10]=1)=[O:9])=[CH:26][CH:25]=2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 27775516-(Trifluoromethyl)nicotinic acidHCID 58126817(2-(Trifluoromethyl)-1h-indol-5-yl)methanamine2×

Product 1

HCID 58138928HCID 58138928, compoundYield 60.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

6-(Trifluoromethyl)nicotinic acid (Sigma-Aldrich; 178 mg, 0.934 mmol) was stirred in DCM (10 mL). Oxalyl chloride (0.131 mL, 1.494 mmol) then DMF (2.89 μl, 0.037 mmol) were added and the reaction mixture was left to stir at room temperature for 2 hrs under Argon. The reaction mixture was evaporated to dryness and the resulting residue was dissolved in DCM (10 mL). A solution of [(2-trifluoromethyl-1H-indol-5-yl)methyl]amine (Intermediate 4, 160 mg, 0.747 mmol) in DCM (10 mL) was added followed by triethylamine (0.208 mL, 1.494 mmol). The reaction mixture was left to stir at room temperature for 1 h. The reaction mixture was evaporated to dryness and the resulting residues where purified by MDAP to give the title compound (176 mg);

Workup

  1. waitthe reaction mixture was left
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutionthe resulting residue was dissolved in DCM (10 mL)
  4. waitThe reaction mixture was left
  5. stirringto stir at room temperature for 1 h
  6. customThe reaction mixture was evaporated to dryness
  7. customthe resulting residues where purified by MDAP

Sources & evidence

ORD record
ord-00b449ec27e6429d95a92942222b4424
Source dataset
uspto-grants-2012_10
Patent number
US08283365B2

Reaction notes

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