3-Amino-1-propanol → HCID 11951289, compound

HRID 1669038Notes

Reaction equation

HRID 1669038 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].Cl[C:7]1[N:8]=[N+:9]([O-:20])[C:10]2[CH:19]=[C:18]3[C:14]([CH2:15][CH2:16][CH2:17]3)=[CH:13][C:11]=2[N:12]=1>COCCOC>[O-:20][N+:9]1[C:10]2[CH:19]=[C:18]3[C:14](=[CH:13][C:11]=2[N:12]=[C:7]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])[N:8]=1)[CH2:15][CH2:16][CH2:17]3

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 160813203-Chloro-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine 1-Oxide

Product 1

HCID 11951289HCID 11951289, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

3-Aminopropanol (0.99 mL, 12.9 mmol) was added to a stirred solution of chloride 21 (956 mg, 4.3 mmol) in DME (80 mL) and the solution stirred at reflux temperature for 6 h. The solvent was evaporated and the residue partitioned between DCM (100 mL) and dilute aqueous NH3 solution (50 mL). The organic fraction was dried and the solvent evaporated. The residue was purified by chromatography, eluting with a gradient (0-10%) of MeOH/DCM, to give 1-oxide 50 (1.09 g, 98%) as a yellow solid: mp (MeOH/DCM) 190-190.5° C.; 1H NMR δ 8.07 (s, 1H, H-9), 7.40 (s, 1H, H-5), 5.61 (br s, 1H, NH), 3.78 (br s, 1H, OH), 3.67-3.73 (m, 4H, CH2O, CH2N), 2.97-3.03 (m, 4H, H-6, H-8), 2.15 (p, J=7.5 Hz, 2H, H-7), 1.82-1.88 (m, 2H, CH2); 13C NMR δ 159.2, 155.0, 147.9, 143.6, 130.0, 120.3, 114.8, 59.0, 37.7, 33.1, 33.0, 32.3, 25.7. Anal. calcd for C13H16N4O2: C, 60.0; H, 6.2; N, 21.5. Found: C, 59.8; H, 6.2; N, 21.6%.

Workup

  1. temperatureat reflux temperature for 6 h
  2. customThe solvent was evaporated
  3. customthe residue partitioned between DCM (100 mL) and dilute aqueous NH3 solution (50 mL)
  4. customThe organic fraction was dried
  5. customthe solvent evaporated
  6. customThe residue was purified by chromatography
  7. washeluting with a gradient (0-10%) of MeOH/DCM

Sources & evidence

ORD record
ord-0f19e95a5aab42728edaa428ab09fd93
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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