Iodoethane → HCID 22380356, compound

HRID 895552Notes

Reaction equation

HRID 895552 reaction equation
[CH:1]([C:4]1[N:9]=[CH:8][C:7]2[N:10]=[C:11]([CH2:13][N:14]3[CH:18]=[CH:17][N:16]=[C:15]3[C:19]3[S:20][CH:21]=[CH:22][N:23]=3)[NH:12][C:6]=2[CH:5]=1)([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].I[CH2:31][CH3:32]>CN(C=O)C.O>[CH2:31]([N:10]1[C:7]2[CH:8]=[N:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][C:6]=2[N:12]=[C:11]1[CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[C:15]1[C:19]1[S:20][CH:21]=[CH:22][N:23]=1)[CH3:32]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 178438402HCID 178438402, compound

Product 1

HCID 22380356HCID 22380356, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-isopropyl-2-(2-thiazol-2-yl-imidazol-1-ylmethyl)-1H-imidazo[4,5-c]pyridine (160 mg, 0.493 mmol) in DMF (1.0 mL) at room temperature under N2 is added Cs2CO3 (168 mg, 0.518 mmol) followed by iodoethane (0.047 mL, 0.592 mmol). The mixture is stirred at room temperature for 1 h and then diluted with water and extracted twice with CH2Cl2. The combined extracts are dried over K2CO3 and concentrated. The residue is purified by preparative TLC, developing with 15:1 CHCl3-MeOH (+0.5% Et3N). The less polar (top) band affords 3-ethyl-6-isopropyl-2-{[2-(1,3-thiazol-2-yl)-1H-imidazol-1-yl]methyl}-3H-imidazo[4,5-c]pyridine. 1H NMR (CDCl3, 300 MHz) δ 8.70 (d, J=1.2 Hz, 1H), 7.83 (d, J=3.0 Hz, 1H), 7.53 (d, J=0.9 Hz, 1H), 7.39 (d, J=3.0 Hz, 1H), 7.18 (d, J=0.9 Hz, 1H), 7.14 (d, J=0.9 Hz, 1H), 6.32 (s, 2H), 4.32 (q, J=7.2 Hz, 2H), 3.18 (sept, J=6.9 Hz, 1H), 1.34 (d, J=6.9 Hz, 6H), 1.17 (t, J=7.2 Hz, 3H) ppm. The more polar (bottom) band affords 74 mg (43%) of 1-ethyl-6-isopropyl-2-{[2-(1,3-thiazol-2-yl)-1H-imidazol-1-yl]methyl}-1H-imidazo[4,5-c]pyridine. 1H NMR (CDCl3, 300 MHz) δ 9.01 (s, 1H), 7.83 (d, J=3.2 Hz, 1H), 7.38 (d, J=3.2 Hz, 1H), 7.15 (8, 1H), 7.12 (s, 1H), 7.09 (s, 1H), 6.32 (s, 2H), 4.21 (q, J=7.2 Hz, 2H), 3.17 (sept, J=6.8 Hz, 1H), 1.34 (d, J=6.8 Hz, 6H), 1.10 (t, J=7.2 Hz, 3H) ppm.

Workup

  1. extractionextracted twice with CH2Cl2
  2. dry with materialThe combined extracts are dried over K2CO3
  3. concentrationconcentrated
  4. customThe residue is purified by preparative TLC

Sources & evidence

ORD record
ord-564c88942f044558a2fbb5d5d00e63d4
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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