Diisopropylethylamine → HCID 68584630, compound

HRID 17483Notes

Reaction equation

HRID 17483 reaction equation
Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:19]#[N:20])[C:8]([CH3:18])=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:10]=2[F:11])[N:6]=1.C(N(CC)C(C)C)(C)C.[OH:30][C:31]1([CH3:35])[CH2:34][NH:33][CH2:32]1>C(Cl)(Cl)Cl>[F:11][C:10]1[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:8]([CH3:18])[C:7]([C:19]#[N:20])=[C:5]2[C:4]=1[O:3][C:2]([N:33]1[CH2:34][C:31]([OH:30])([CH3:35])[CH2:32]1)=[N:6]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 115427823-Methylazetidin-3-olHCID 510414292-Chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 68584630HCID 68584630, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

Under nitrogen atmosphere, 2-chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (216 mg, 0.753 mmol) was dissolved in N,N-dimethylsulfoamide (10 ml), then N,N-diisopropylethylamine (584 μl, 3.35 mmol) and 3-hydroxy-3-methylazetidine (132 mg, 1.51 mmol) dissolved in N,N-dimethylsulfoamide (5 ml) were added, followed by stirring under heat at 100° C. for 20 hours. After cooling, diluting with chloroform and washing with water, the organic layer was dried over anhydrous magnesium, sulfate, then the solvent was evaporated away under reduced pressure. The resulting residue was subjected to preparative silica gel column chromatography. The eluate with chloroform/methanol (10:1, v/v) gave the entitled compound (234 mg, 92%) as a white solid.

Workup

  1. additionwere added
  2. temperatureAfter cooling
  3. washwashing with water
  4. dry with materialthe organic layer was dried over anhydrous magnesium, sulfate
  5. customthe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-21675023213a4610ba4c4e9da763fe5f
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

Loading…