Triethylamine hydrochloride → HCID 178420382, compound

HRID 270933Notes

Reaction equation

HRID 270933 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[N:17][C:18]3[N:19]([N:27]=[CH:28][C:29]=3[C:30]#[N:31])[C:20]=2[N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(N(CC)CC)C.[N-:40]=[N+:41]=[N-:42].[Na+]>C1(C)C=CC=CC=1.CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[N:17][C:18]3[N:19]([N:27]=[CH:28][C:29]=3[C:30]3[NH:42][N:41]=[N:40][N:31]=3)[C:20]=2[N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11130Triethylamine hydrochloride2×HCID 33557Sodium Azide2×HCID 18445877HCID 18445877, compound

Product 1

HCID 178420382HCID 178420382, compoundYield 38.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

According to a modification of a literature procedure (Herr, R. J. Bioorg. Med. Chem. 2002, 10, 3379-3393) a solution of 35 mg (0.085 mmol) of 6-(4-benzyloxy-phenyl)-7-morpholin-4-yl-pyrazolo[1,5-a]pyrimidine-3-carbonitrile in 1.5 mL of toluene and 0.5 mL of dimethylformamide was added 71 mg (0.513 mmol) of triethylamine hydrochloride (Et3N—HCl), and 33 mg (0.513 mmol) of sodium azide and the resulting heterogeneous mixture was heated at reflux for 72 h, during which time 71 mg (0.513 mmol) of triethylamine hydrochloride (Et3N—HCl), and 33 mg (0.513 mmol) of sodium azide was added to the reaction mixture after every 24 h. The mixture was then cooled to rt, filtered and concentrated to a residue which was purified via reverse-phase chromatography to afford (after lyophilization) 15 mg (38% yield) of 6-(4-benzyloxy-phenyl)-7-morpholin-4-yl-3-(1H-tetrazol-5-yl)-pyrazolo[1,5-a]pyrimidine (370) as a solid as indicated by 1H-NMR. (LC-MS calcd for C24H22N8O2 [M+H]+455.18; found 455.2.

Workup

  1. temperaturethe resulting heterogeneous mixture was heated
  2. additionwas added to the reaction mixture after every 24 h
  3. filtrationfiltered
  4. concentrationconcentrated to a residue which
  5. customwas purified via reverse-phase chromatography

Sources & evidence

ORD record
ord-6085418da7b94458ab1f7ae5290045e1
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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