Water → HCID 21875822, compound

HRID 858413Notes

Reaction equation

HRID 858413 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][N:21]=[N+]=[N-])=[CH:15][CH:14]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:24])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([C:13]3[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][NH2:21])=[CH:15][CH:14]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:24])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 21876167HCID 21876167, compound

Product 1

HCID 21875822HCID 21875822, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-[4-(5-chloro-2-ethyl-7-methyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl]ethyl azide (step 6, 57 mg, 0.2 mmol) in THF (5 mL,) was added triphenylphosphine (47 mg, 0.2 mmol) at room temperature. After completion of the addition, the stirring was continued for an additional 3 h at the same temperature. To the resulting mixture was added water (0.1 mL) at room temperature, and the reaction mixture was stirred at room temperature for 20 h. The mixture was concentrated to give colorless solids. Purification by preparative TLC (dichloromethane/methanol/triethylamine=10:1:1) gave 13 mg (25%) of the title compound as colorless solids: MS (EI) m/z 313 (M+).

Workup

  1. additionAfter completion of the addition
  2. concentrationThe mixture was concentrated
  3. customto give colorless solids
  4. customPurification by preparative TLC (dichloromethane/methanol/triethylamine=10:1:1)

Sources & evidence

ORD record
ord-cc4ddbac131e42f898dc1983302743d2
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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