tert-Butyl methyl ether → HCID 86634374, compound

HRID 1191275Notes

Reaction equation

HRID 1191275 reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:3]1[CH2:14][N:15]=[N+:16]=[N-:17].Cl[C:19]1[N:24]=[C:23]([N:25]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:22]=[CH:21][N:20]=1.COC(C)(C)C>C1(O)CCCCC1>[N:25]1([C:23]2[CH:22]=[CH:21][N:20]=[C:19]([NH:1][C@H:2]3[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:12])([CH3:13])[CH3:11])=[O:8])[C@@H:3]3[CH2:14][N:15]=[N+:16]=[N-:17])[N:24]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 151757481-(2-Chloropyrimidin-4-yl)azepaneHCID 86634373HCID 86634373, compound

Product 1

HCID 86634374HCID 86634374, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 7966CyclohexanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of the compound 7 (240 mg) in cyclohexanol (0.4 mL), 1-(2-chloro-4-pyrimidinyl)azepane (210 mg) was added. The reaction mixture was stirred at 120° C. for 3.5 hours. After cooling to room temperature, the reaction mixture was added tert-butyl methyl ether, washed with aqueous 2N sodium hydroxide solution, dried over anhydrous magnesium sulfate and then concentrated. The obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol:27% aqueous ammonia=100:0:0→90:10:0→90:10:1) to obtain the title compound (190 mg) having the following physical properties.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with aqueous 2N sodium hydroxide solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol:27% aqueous ammonia=100:0:0→90:10:0→90:10:1)

Sources & evidence

ORD record
ord-ad2ff19fed9d453387f676f18eab6127
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

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