Diisopropylethylamine → HCID 68283198, compound

HRID 624063Notes

Reaction equation

HRID 624063 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[O:11][CH:10]=[N:9][C:8]=2[C:12]([OH:14])=O)[CH:2]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:47][C:48]1[CH:49]=[N:50][N:51]([CH2:53][CH2:54][OH:55])[CH:52]=1>C(Cl)Cl.O.CN(C=O)C>[OH:55][CH2:54][CH2:53][N:51]1[CH:52]=[C:48]([NH:47][C:12]([C:8]2[N:9]=[CH:10][O:11][C:7]=2[C:3]2[CH:2]=[C:1]([CH3:15])[CH:6]=[CH:5][CH:4]=2)=[O:14])[CH:49]=[N:50]1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 284922672-(4-Amino-1H-pyrazol-1-yl)ethanolHCID 299230925-(m-Tolyl)oxazole-4-carboxylic acid

Product 1

HCID 68283198HCID 68283198, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 5-(m-tolyl)oxazole-4-carboxylic acid (5.50 g, 27.07 mmol) in DCM (80 mL), TBTU (13.04 g, 40.60 mmol) and DIPEA (13.90 mL, 81.20 mmol) was added. After stirring for 40 min at rt, 2-(4-amino-1H-pyrazol-1-yl)ethanol (3.47 g, 27.07 mmol) dissolved in DCM (10 mL) and DMF (4 mL) was added to the reaction mixture and stirred at rt for 1 h, then the reaction mixture was diluted with DCM and water, the org. layer was separated and the aq. layer extracted with DCM (1×). The combined org. layers were washed with brine, dried (MgSO4), filtered and the solvent was removed under reduced pressure. Purification by FC (DCM/MeOH, 95:5 to DCM/MeOH 9:1) yielded the tiltle compound as a white solid. LC-MS conditions A: tR=0.71 min, [M+H]+=313.44.

Workup

  1. stirringstirred at rt for 1 h
  2. customlayer was separated
  3. extractionthe aq. layer extracted with DCM (1×)
  4. washlayers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customPurification by FC (DCM/MeOH, 95:5 to DCM/MeOH 9:1)

Sources & evidence

ORD record
ord-0363448fe3a5466e9c68a1c6801143ad
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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