2-Methylimidazole → HCID 9911458, compound

HRID 1359454Notes

Reaction equation

HRID 1359454 reaction equation
C(OC([NH:8][C:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:23]([Cl:24])=[CH:22][N:21]=[C:20]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([CH2:32][CH2:33]O)=[CH:28][CH:27]=3)[N:19]=2)=[CH:14][CH:13]=1)([CH3:11])[CH3:10])=O)(C)(C)C.C(N(C(C)C)CC)C.[CH3:43][C:44]1[NH:45][CH:46]=[CH:47][N:48]=1.C([NH+](CC)CC)C>C(#N)C.O1CCCC1>[NH2:8][C:9]([C:12]1[CH:13]=[CH:14][C:15]([C:18]2[C:23]([Cl:24])=[CH:22][N:21]=[C:20]([NH:25][C:26]3[CH:27]=[CH:28][C:29]([CH2:32][CH2:33][N:45]4[CH:46]=[CH:47][N:48]=[C:44]4[CH3:43])=[CH:30][CH:31]=3)[N:19]=2)=[CH:16][CH:17]=1)([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 127492-MethylimidazoleHCID 521913N,N-Diethyl-2-propanamineHCID 1385867TriethylammoniumHCID 18183227HCID 18183227, compound

Product 1

HCID 9911458HCID 9911458, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of derivatised resin (1) (55 mg), N,N-diethylisopropylamine (38 mg, 0.30 mmol), and 2-methylimidazole (8 mg, 0.10 mmol) in anhydrous acetonitrile (2 ml) was heated at 70° for 18 h, with agitation. The mixture was allowed to cool to room temperature then diluted with anhydrous tetrahydrofuran (2 ml) and treated with polystyrene methylisocyanate (Argonaut Technologies, 120 mg, 1.65 mmol/g, 0.2 mmol equivalent) and macroporous triethylammonium methylpolystyrene carbonate (Argonaut Technologies, 38 mg, 2.64 mmol/g, 0.1 mmol equivalent). The resulting mixture was agitated at room temperature for 6 h, then filtered and washed once with dichloromethane. The combined filtrate and washings were evaporated to dryness under a stream of nitrogen, then resuspended in dichloromethane (1 mL) and treated with trifluoroacetic acid (1 mL) for 1 h at room temperature. The mixture was evaporated to give the title compound (19.4 mg).

Workup

  1. temperaturewas heated at 70° for 18 h, with agitation
  2. filtrationfiltered
  3. washwashed once with dichloromethane
  4. customThe combined filtrate and washings were evaporated to dryness under a stream of nitrogen
  5. additiontreated with trifluoroacetic acid (1 mL) for 1 h at room temperature
  6. customThe mixture was evaporated

Sources & evidence

ORD record
ord-8cacae8b5e1f4469a5779b164cff6d69
Source dataset
uspto-grants-2003_07
Patent number
US06600037B1

Reaction notes

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