Triethylamine hydrochloride → HCID 178492642, compound

HRID 545175Notes

Reaction equation

HRID 545175 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Cl.C(N(CC)CC)C.[CH3:13][O:14][C:15]1[C:24]2[C:19](=[C:20]([O:25][CH3:26])[CH:21]=[CH:22][CH:23]=2)[N:18]=[C:17]([C:27]([N:29]2[CH2:34][CH2:33][C:32]3([CH2:43][C:42](=[O:44])[C:41]4[C:36](=[CH:37][CH:38]=[C:39]([C:45]#[N:46])[CH:40]=4)[O:35]3)[CH2:31][CH2:30]2)=[O:28])[CH:16]=1.[OH-].[Na+]>O.CN(C=O)C>[CH3:13][O:14][C:15]1[C:24]2[C:19](=[C:20]([O:25][CH3:26])[CH:21]=[CH:22][CH:23]=2)[N:18]=[C:17]([C:27]([N:29]2[CH2:34][CH2:33][C:32]3([CH2:43][C:42](=[O:44])[C:41]4[C:36](=[CH:37][CH:38]=[C:39]([C:45]5[NH:46][N:3]=[N:2][N:1]=5)[CH:40]=4)[O:35]3)[CH2:31][CH2:30]2)=[O:28])[CH:16]=1

Participants

7

Reactant 4

HCID 11130Triethylamine hydrochlorideHCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 16041932HCID 16041932, compound

Product 1

HCID 178492642HCID 178492642, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Alternatively, 195 mg of sodium azide, 413 mg of triethylamine hydrochloride and 5 mL of DMF were added to the nitrile derivative (458 mg) produced in Example 16, and stirred at 100° C. under a nitrogen atmosphere for 20 hours. After cooled, the mixture was added by 30 mL of water and 0.60 mL of aqueous 5 N sodium hydroxide solution, then the mixture was washed five times with chloroform (10 mL each). 0.60 mL of 5 N hydrochloric acid was added to the aqueous layer, and the mixture was extracted with chloroform. The extract was washed with saturated brine, dried over sodium sulfate, and concentrated. The resulting residue was purified through silica gel chromatography (chloroform/methanol=50/1 to 30/1, chloroform/methanol/acetic acid=300/100/1), the fraction containing it was concentrated, and ethyl ether was added to the residue. The resulting insoluble material was taken out through filtration, washed with ethyl ether, and dried under reduced pressure to obtain the intended compound as a pale yellow powder. 1H-NMR (300 MHz, DMSO-d6) δ: 8.44 (1H, d, J=2.3 Hz), 8.26 (1H, dd, J=8.6, 2.3 Hz), 7.69 (1H, dd, J=8.4, 1.1 Hz), 7.53 (1H, dd, J=8.4, 7.8 Hz), 7.38 (1H, d, J=8.6 Hz), 7.25 (1H, dd, J=7.8, 1.1 Hz), 7.21 (1H, s), 4.38-4.30 (1H, m), 4.08 (3H, s), 3.95 (3H, s), 3.70-3.62 (1H, m), 3.52-3.43 (1H, m), 3.38-3.28 (1H, m), 3.02 (2H, s), 2.15-2.08 (1H, m), 1.99-1.82 (3H, m). MS [M+H]+=501

Workup

  1. temperatureAfter cooled
  2. washthe mixture was washed five times with chloroform (10 mL each)
  3. addition0.60 mL of 5 N hydrochloric acid was added to the aqueous layer
  4. extractionthe mixture was extracted with chloroform
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe resulting residue was purified through silica gel chromatography (chloroform/methanol=50/1 to 30/1, chloroform/methanol/acetic acid=300/100/1)
  9. additionthe fraction containing it
  10. concentrationwas concentrated
  11. additionethyl ether was added to the residue
  12. filtrationThe resulting insoluble material was taken out through filtration
  13. washwashed with ethyl ether
  14. customdried under reduced pressure

Sources & evidence

ORD record
ord-59e0a128698b4721a5e42e78349323c7
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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