Diisopropylethylamine → HCID 46941028, compound

HRID 2114362Notes

Reaction equation

HRID 2114362 reaction equation
[CH3:1][C:2]1[C:15]([O:16][CH3:17])=[CH:14][C:5]2[N:6]([CH2:10][C:11]([OH:13])=O)[C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[C:54]1([C:70]2[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=2)[CH:59]=[CH:58][C:57]([CH:60]([NH:68][CH3:69])[CH2:61][N:62]2[CH2:67][CH2:66][O:65][CH2:64][CH2:63]2)=[CH:56][CH:55]=1>C(Cl)Cl>[C:54]1([C:70]2[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=2)[CH:55]=[CH:56][C:57]([CH:60]([N:68]([CH3:69])[C:11](=[O:13])[CH2:10][N:6]2[C:5]3[CH:14]=[C:15]([O:16][CH3:17])[C:2]([CH3:1])=[CH:3][C:4]=3[O:8][C:7]2=[O:9])[CH2:61][N:62]2[CH2:63][CH2:64][O:65][CH2:66][CH2:67]2)=[CH:58][CH:59]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 57425536[1-(4-Biphenylyl)-2-(4-morpholinyl)ethyl]methylamineHCID 57457148[6-Methyl-5-(methyloxy)-2-oxo-1,3-benzoxazol-3(2H)-yl]acetic acid

Product 1

HCID 46941028HCID 46941028, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[6-Methyl-5-(methyloxy)-2-oxo-1,3-benzoxazol-3(2H)-yl]acetic acid (59 mg, 0.25 mmol) and BOP reagent (133 mg, 0.30 mmol) were dissolved in CH2Cl2 (1 mL), and diisopropylethylamine (32 mg, 0.25 mmol) was added. The resulting mixture was stirred at room temperature for 5 min, then 1-(4-biphenylyl)-N-methyl-2-(4-morpholinyl)ethanamine (74 mg, 0.25 mmol) was added. Stirring was continued for 16 h and then the mixture was concentrated. The residue was dissolved in CH3OH, and purified by preparative HPLC (YMC CombiPrep ODS-A, 50×50 mm, 50 mL/min, A: acetonitrile B: water with NH4OH at pH=10, A: 20% to 70% during 12 min, UV detection at 214 nm) to give 32 mg (25%) of the title compound as a white solid. MS (ES) m/e 516 [M+H]+.

Workup

  1. stirringStirring
  2. waitwas continued for 16 h
  3. concentrationthe mixture was concentrated
  4. dissolutionThe residue was dissolved in CH3OH
  5. custompurified by preparative HPLC (YMC CombiPrep ODS-A, 50×50 mm, 50 mL/min
  6. waitA: acetonitrile B: water with NH4OH at pH=10, A: 20% to 70% during 12 min

Sources & evidence

ORD record
ord-5c1ccd20559c4599906d87712eeb71f9
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

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