Triethylamine → HCID 45095725, compound

HRID 860032Notes

Reaction equation

HRID 860032 reaction equation
[CH:1]1([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12](C(O)=O)[CH:13]=3)[C:8]([CH2:18][CH3:19])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([N:22](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>C(O)(C)(C)C>[NH2:22][C:12]1[CH:13]=[C:14]2[C:9]([C:8]([CH2:18][CH3:19])=[N:7][N:6]2[CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 15545851HCID 15545851, compound

Product 1

HCID 45095725HCID 45095725, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 1-cyclopentyl-3-ethyl-1H-indazole-6-carboxylic acid (258 mg) and triethylamine (0.56 mL) in t-butanol (1 ml) was added diphenylphosphoryl azide (0.33 μL). The mixture was stirred at 100° C. for 4 h, then partitioned between water (25 mL) and ether (25 mL). The ether layer was collected, dried (MgSO4), and passed through a plug of silica. The silica was washed with an additional 25 mL of ether and the mixture was concentrated in vacuo. The residue was dissolved in THF (5 mL) and 6N aq. HCL (1 mL) was added and the mixture was stirred for 18 h. Ether (25 mL) and water (25 mL) were added and the ether layer was collected, dried (MgSO4), and concentrated in vacuo. The residue was purified by column chromatography on silica gel to yield 0.14 g of 6-amino-1-cyclopentyl-3-ethyl-1H-indazole (59% yield). 1H NMR (300 MHz) δ 7.45 (d,J=8.4 Hz, 1H), 6.52 (m,2H), 4.74 (p,J=7.8 Hz, 1H), 3.86 (br,2H), 2.95 (q,J=7.7 Hz,2H), 2.3–1.8 (m,6H), 1.8–1.6 (m,2H), 1.37 (t,J=7.7 Hz,3H).

Workup

  1. custompartitioned between water (25 mL) and ether (25 mL)
  2. customThe ether layer was collected
  3. dry with materialdried (MgSO4)
  4. washThe silica was washed with an additional 25 mL of ether
  5. concentrationthe mixture was concentrated in vacuo
  6. dissolutionThe residue was dissolved in THF (5 mL)
  7. addition6N aq. HCL (1 mL) was added
  8. stirringthe mixture was stirred for 18 h
  9. additionEther (25 mL) and water (25 mL) were added
  10. customthe ether layer was collected
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated in vacuo
  13. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1d56582893a745768bfebe3a97bd27b6
Source dataset
uspto-grants-2006_12
Patent number
US07153871B2

Reaction notes

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