Diisopropylethylamine → HCID 69928415, compound

HRID 536996Notes

Reaction equation

HRID 536996 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH2:7])=[N:3]1.CCN(C(C)C)C(C)C.[C:17]([O:21][C:22]([NH:24][C:25]1([CH:31]([OH:35])[C:32](O)=[O:33])[CH2:28][C:27]([F:30])([F:29])[CH2:26]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:17]([O:21][C:22](=[O:23])[NH:24][C:25]1([CH:31]([OH:35])[C:32](=[O:33])[NH:7][C:4]2[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=2)[CH2:28][C:27]([F:29])([F:30])[CH2:26]1)([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1372541-Methyl-3-aminopyrazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67229995HCID 67229995, compound

Product 1

HCID 69928415HCID 69928415, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Methyl-1H-pyrazol-3-amine (158 mg, 1.63 mmol) and DIEA (1.08 mL, 6.52 mmol) was added to a solution of (1-tert-Butoxycarbonylamino-3,3-difluoro-cyclobutyl)-hydroxy-acetic acid (1.63 mmol) dissolved in DMF (20 mL). The solution was cooled to 0° C. and after 10 minutes HATU (620 mg, 1.63 mmol) was added. After approximately 2 hours at RT, LC-MS showed product and no starting material and the solvent was removed by rotary evaporation. The crude product was dissolved in 40 mL EtOAc and washed with 25 mL sat. NaHCO3 (aq). The organic phase was dried with Na2SO4, filtered and evaporated to dryness. The crude product was purified on a 25 g silica column on a Biotage Flashmaster, which gave the title product as a white solid (92%). TLC rf: 0.07 in heptane:ethyl acetate 1:1.

Workup

  1. additionwas added
  2. customno starting material and the solvent was removed by rotary evaporation
  3. dissolutionThe crude product was dissolved in 40 mL EtOAc
  4. washwashed with 25 mL sat. NaHCO3 (aq)
  5. dry with materialThe organic phase was dried with Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe crude product was purified on a 25 g silica column on a Biotage Flashmaster, which

Sources & evidence

ORD record
ord-e00331dd946e40d28f7dd8468029d2b8
Source dataset
uspto-grants-2014_10
Patent number
US08859605B2

Reaction notes

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