Diisopropylethylamine → HCID 86704223, compound

HRID 624072Notes

Reaction equation

HRID 624072 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.[C:16]([O:20][C:21](=[O:31])[NH:22][CH2:23][CH2:24][N:25]1[CH:29]=[C:28]([NH2:30])[CH:27]=[N:26]1)([CH3:19])([CH3:18])[CH3:17].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.O>[C:16]([O:20][C:21](=[O:31])[NH:22][CH2:23][CH2:24][N:25]1[CH:29]=[C:28]([NH:30][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:27]=[N:26]1)([CH3:19])([CH3:17])[CH3:18]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 299230925-(m-Tolyl)oxazole-4-carboxylic acidHCID 709843161394162-48-1

Product 1

HCID 86704223HCID 86704223, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(m-tolyl)oxazole-4-carboxylic acid (1.60 g, 7.87 mmol) in DCM (15 mL), tert-butyl(2-(4-amino-1H-pyrazol-1-yl)ethyl)carbamate (1.80 g, 7.96 mmol), DIPEA (6.8 mL, 39.86 mmol) and HATU (7.485 g, 19.69 mmol) was added. After stirring the reaction mixture at rt for 18 h, the reaction mixture was diluted with DCM and H2O. The org. layer was separated and the aq. layer was extracted with DCM (3×). The combined org. layers wered dried (MgSO4), filtered and the solvent was removed under reduced pressure. Purification by FC (EtOA/hex 3:7 to 1:1) yielded tert-butyl(2-(4-(5-(m-tolyl)oxazole-4-carboxamido)-1H-pyrazol-1-yl)ethyl)carbamate as a white solid. LC-MS conditions B: tR=0.8 min, [M+H]+=412.46.

Workup

  1. customlayer was separated
  2. extractionthe aq. layer was extracted with DCM (3×)
  3. dry with materiallayers wered dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification by FC (EtOA/hex 3:7 to 1:1)

Sources & evidence

ORD record
ord-da02189e22c64de0a1d62b76eb847237
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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