1-Butanol → HCID 178461872, compound

HRID 475220Notes

Reaction equation

HRID 475220 reaction equation
Cl.O1CCCCC1[N:8]1[C:12]2[CH:13]=[CH:14][C:15]([C@@H:17]([NH2:19])[CH3:18])=[CH:16][C:11]=2[N:10]=[CH:9]1.Cl[C:21]1[N:26]=[C:25]([NH:27][C:28]2[NH:32][N:31]=[C:30]([CH:33]3[CH2:35][CH2:34]3)[CH:29]=2)[CH:24]=[CH:23][N:22]=1.CCCCO.CCN(C(C)C)C(C)C>CCOC(C)=O.CO.O>[NH:8]1[C:12]2[CH:13]=[CH:14][C:15]([C@@H:17]([NH:19][C:21]3[N:26]=[C:25]([NH:27][C:28]4[CH:29]=[C:30]([CH:33]5[CH2:35][CH2:34]5)[NH:31][N:32]=4)[CH:24]=[CH:23][N:22]=3)[CH3:18])=[CH:16][C:11]=2[N:10]=[CH:9]1

Participants

8

Reactant 4

HCID 2631-ButanolHCID 81531DiisopropylethylamineHCID 86694728HCID 86694728, compoundHCID 178478345HCID 178478345, compound

Product 1

HCID 178461872HCID 178461872, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A 5 mL microwave tube was charged with 126 (208.2 mg, 0.85 mmol), 53 (100 mg, 0.42 mmol) and n-BuOH (1.2 mL) then DIPEA (0.371 mL) was added, the tube sealed and heated to 140° C. for 18 h in an oil bath. The reaction cooled and diluted with EtOAc (50 mL). Water (25 mL) and some MeOH (1 mL) were added and the phases were separated. The organic layer was washed with brine (25 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by HPLC and SFC to afford 34.4 mg (22%) of I-5 as a white solid: SFC RT=0.72 min.

Workup

  1. customthe tube sealed
  2. temperatureThe reaction cooled
  3. customthe phases were separated
  4. washThe organic layer was washed with brine (25 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by HPLC and SFC
  9. customto afford 34.4 mg (22%) of I-5 as a white solid

Sources & evidence

ORD record
ord-46d0bb890f4a419f95b06bd43643b7ce
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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