Dipropylamine → HCID 14390311, compound

HRID 2351700Notes

Reaction equation

HRID 2351700 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]([NH:39][CH2:40][CH2:41][CH3:42])[CH2:37][CH3:38]>O1CCCC1>[CH2:36]([N:39]([CH2:40][CH2:41][CH3:42])[C:19](=[O:21])[CH2:18][N:17]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[N:10]=[C:9]1[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:23])([F:1])[F:22])=[CH:8][CH:7]=1)[CH2:37][CH3:38]

Participants

5

Reactant 3

HCID 8902DipropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 15617192HCID 15617192, compound

Product 1

HCID 14390311HCID 14390311, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 2-(4-trifluoromethylphenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (3.21 g, 0.010 mole), and 1,1'-carbonyldiimidazole (1.62 g, 0.010 mole), in anhydrous tetrahydrofurn (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 dipropylamine (1.31 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 twice from isopropyl ether-petroleum ether, giving 1.26 g (31%) of a white solid, mp 138°-139° 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 twice from isopropyl ether-petroleum ether

Sources & evidence

ORD record
ord-9f7bf15d364046c18a430fde201d31fe
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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