Water → HCID 22007010, compound

HRID 917519Notes

Reaction equation

HRID 917519 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])[N:14]=2)[CH2:5][CH2:4]1.I[CH:24]([CH3:26])[CH3:25].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH:24]([NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([NH:9][C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])[N:14]=2)[CH2:5][CH2:4]1)([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 15524262HCID 15524262, compound

Product 1

HCID 22007010HCID 22007010, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

The reaction mixture of N-[4-(aminomethyl)cyclohexyl]-4-(2-methoxyphenyl)-1,3-thiazol-2-amine (1 equivalent), 2-iodopropane (1 equivalent), and potassium carbonate (2 equivalents) in DMF was heated at about 50° C. overnight. Water was then added to the reaction mixture and extracted with diethyl ether (3 times). Evaporation of the combined organic phase afforded a yellow oil which was purified by preparative TLC plates. The desired product was obtained as a yellow oil in 53% yield: ESIMS m/e=360 (MH+).

Workup

  1. extractionextracted with diethyl ether (3 times)
  2. customEvaporation of the combined organic phase
  3. customafforded a yellow oil which
  4. customwas purified by preparative TLC plates

Sources & evidence

ORD record
ord-423ec3b1de654e48827fb2014352cb51
Source dataset
uspto-grants-2007_09
Patent number
US07273880B2

Reaction notes

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