Benzylamine → HCID 14390312, compound

HRID 2073027Notes

Reaction equation

HRID 2073027 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:17]([CH2:18][C:19]([OH:21])=O)[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[N:10]=2)=[CH:5][CH:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:36]([NH2:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O1CCCC1>[C:37]1([CH2:36][NH:43][C:19](=[O:21])[CH2:18][N:17]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[N:10]=[C:9]2[C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:23])([F:22])[F:1])=[CH:4][CH:5]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 15617192HCID 15617192, compound

Product 1

HCID 14390312HCID 14390312, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-(4-trifluoromethylphenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (3.21 g, 0.010 mole), 1,1'-carbonyldiimidazole (1.62 g, 0.010 mole), and anhydrous tetrahydrofuran (75 ml) was stirred at room temperature with a stream of nitrogen bubbling through for 3 hours. The nitrogen flow was stopped and a solution of benzylamine (1.39 g, 0.013 mole) in dry tetrahydrofuran (25 ml) was added. The solution was stirred at room temperature under nitrogen for 1 hour. The reaction mixture was concentrated in vacuo and the residue triturated in potassium bicarbonate solution (50 ml) and filtered. The filter cake was washed with water and recrystallized from isopropyl alcohol-isopropyl ether, giving 2.8 g (68%). Recrystallization from isopropyl alcoholisopropyl ether gave 2.3 g of white flakes, mp 224°-225° C.

Workup

  1. stirringThe solution was stirred at room temperature under nitrogen for 1 hour
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue triturated in potassium bicarbonate solution (50 ml)
  4. filtrationfiltered
  5. washThe filter cake was washed with water
  6. customrecrystallized from isopropyl alcohol-isopropyl ether
  7. customgiving 2.8 g (68%)
  8. customRecrystallization from isopropyl alcoholisopropyl ether
  9. customgave 2.3 g of white flakes, mp 224°-225° C.

Sources & evidence

ORD record
ord-d91d34a59ca84f28890f3fd1cf13f708
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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