Diisopropylethylamine → HCID 66769667, compound

HRID 1025268Notes

Reaction equation

HRID 1025268 reaction equation
[CH:1]1([C:7]2[O:8][C:9]3[CH:15]=[C:14]([C:16]([OH:18])=O)[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH:52]1[CH2:55][CH:54]([OH:56])[CH2:53]1>CN(C=O)C>[CH:1]1([C:7]2[O:8][C:9]3[CH:15]=[C:14]([C:16]([N:52]4[CH2:55][CH:54]([OH:56])[CH2:53]4)=[O:18])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 15142903-HydroxyazetidineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66771669HCID 66771669, compound

Product 1

HCID 66769667HCID 66769667, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-cyclohexyl-benzooxazole-6-carboxylic acid (0.47 g, 1.9 mmol) and HBTU (0.94 g, 2.5 mmol) in DMF (10 mL) was added DIPEA (1.4 mL, 7.6 mmol). The resulting mixture was stirred at room temperature for 10 min, and then the hydrochloride salt of azetidin-3-ol (0.452 g, 4.7 mmol) was added. The resulting mixture was stirred at room temperature for 1 h, and then purified by reverse phase liquid chromatography. Fractions containing product were lyophilized to yield (2-cyclohexyl-benzooxazol-6-yl)-(3-hydroxy-azetidin-1-yl)-methanone. MS m/z (M+H+) 301.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 1 h
  2. custompurified by reverse phase liquid chromatography
  3. additionFractions containing product

Sources & evidence

ORD record
ord-ea8b3c5b741a46869678ecfa5fff2df6
Source dataset
uspto-grants-2014_05
Patent number
US08729064B2

Reaction notes

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