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Diisopropylethylamine → (R)-2-phenoxymethyl-5-(1,2,2-trimethyl-propyl)-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one

HRID 2046222
Notes
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Reaction equation

HRID 2046222 reaction equation
[O:1]([CH2:8][C:9]1[CH:10]=[C:11]([C:23](O)=[O:24])[N:12]([CH2:14][CH2:15][NH:16][C@H:17]([CH3:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[O:1]([CH2:8][C:9]1[CH:10]=[C:11]2[C:23](=[O:24])[N:16]([C@H:17]([CH3:22])[C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:15][CH2:14][N:12]2[N:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67976139HCID 67976139, compound

Product 1

HCID 67991611(R)-2-phenoxymethyl-5-(1,2,2-trimethyl-propyl)-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-oneYield 17%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

A mixture of (R)-5-phenoxymethyl-2-[2-(1,2,2-trimethyl-propylamino)-ethyl]-2H-pyrazole-3-carboxylic acid (130 mg, 0.38 mmol) and HATU (143 mg, 0.38 mmol) in DMF (3 mL) was stirred for 5 minutes at room temperature, then DIPEA (0.16 mL, 0.945 mmol) were added. The reaction mixture was stirred at room temperature for 16 hours and then washed with a saturated solution of NH4Cl and extracted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The residue was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 20/80). The desired fractions were collected and the solvents evaporated in vacuo. The desired product was triturated with diethyl ether to yield (R)-2-phenoxymethyl-5-(1,2,2-trimethyl-propyl)-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (21 mg, 17% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ ppm 0.98 (s, 9H), 1.21 (d, J=7.2 Hz, 3H), 3.66-3.79 (m, 2H), 4.27-4.40 (m, 2H), 4.73 (q, J=7.2 Hz, 1H), 5.09 (s, 2H), 6.93 (s, 1H), 6.96 (t, J=7.4 Hz, 1H), 7.00 (d, J=7.8 Hz, 2H), 7.27-7.32 (m, 2H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 16 hours
  2. washwashed with a saturated solution of NH4Cl
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvents evaporated in vacuo
  8. customThe residue was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 20/80)
  9. customThe desired fractions were collected
  10. customthe solvents evaporated in vacuo
  11. customThe desired product was triturated with diethyl ether

Sources & evidence

ORD record
ord-e20f76f7d2504871acd5a1d1210bed2c
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08592422B2

Reaction notes

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