Diisopropylethylamine → N-(1-(2,2-dimethoxyethyl)-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide

HRID 624084Notes

Reaction equation

HRID 624084 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(O[N:24]1[N:32]=[N:31][C:26]2C=CC=[CH:30][C:25]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:47][O:48][CH:49]([O:58][CH3:59])[CH2:50]CN1C=C(N)C=N1>C(Cl)Cl.O.CN(C=O)C>[CH3:47][O:48][CH:49]([O:58][CH3:59])[CH2:50][N:31]1[CH:26]=[C:25]([NH:24][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:30]=[N:32]1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 299230925-(m-Tolyl)oxazole-4-carboxylic acidHCID 867042311-(3,3-dimethoxypropyl)-1H-pyrazol-4-amine

Product 1

HCID 86704230N-(1-(2,2-dimethoxyethyl)-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 5-(m-tolyl)oxazole-4-carboxylic acid (5.34 g, 26.28 mmol) in DCM (135 mL), TBTU (12.66 g, 39.42 mmol) and DIPEA (13.50 mL, 78.84 mmol) was added. After stirring for 30 min at rt, 1-(3,3-dimethoxypropyl)-1H-pyrazol-4-amine (4.50 g, 26.29 mmol) dissolved in DCM (15 mL) and DMF (2 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 (EtOAc/hept 7:3) yielded N-(1-(2,2-dimethoxyethyl)-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide as a pale yellow solid. LC-MS conditions A: tR=0.82 min, [M+H]+=357.06.

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 (EtOAc/hept 7:3)

Sources & evidence

ORD record
ord-09fa571a3f7544a08154fdca500cda5e
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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