Triethylamine hydrochloride → HCID 178504666, compound

HRID 270940Notes

Reaction equation

HRID 270940 reaction equation
[CH:1]1([C:7]2[N:12]3[N:13]=[CH:14][C:15]([C:16]#[N:17])=[C:11]3[N:10]=[CH:9][C:8]=2[C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C(N(CC)CC)C.[N-:42]=[N+:43]=[N-:44].[Na+]>C1(C)C=CC=CC=1.CN(C)C=O>[CH:1]1([C:7]2[N:12]3[N:13]=[CH:14][C:15]([C:16]4[NH:44][N:43]=[N:42][N:17]=4)=[C:11]3[N:10]=[CH:9][C:8]=2[C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:25]=[CH:26][C:27]([S:30]([CH3:33])(=[O:31])=[O:32])=[CH:28][CH:29]=3)=[CH:20][CH:19]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 11130Triethylamine hydrochloride2×HCID 33557Sodium Azide2×HCID 18445886HCID 18445886, compound

Product 1

HCID 178504666HCID 178504666, compoundYield 15.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 42 mg (0.092 mmol) of 7-cyclohexyl-6-(4′-methanesulfonyl-biphenyl-4-yl)-pyrazolo[1,5-a]pyrimidine-3-carbonitrile in 1 mL of toluene and 1.2 mL of dimethylformamide (DMF) was added 76 mg (0.55 mmol) of triethylamine hydrochloride (Et3N—HCl), and 36 mg (0.55 mmol) of sodium azide and the resulting heterogeneous mixture was heated at 120° C. for 72 h, during which time 76 mg (0.55 mmol) of triethylamine hydrochloride (Et3N—HCl), and 36 mg (0.55 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) 7 mg (15% yield) of 7-cyclohexyl-6-(4′-methanesulfonyl-biphenyl-4-yl)-3-(1H-tetrazol-5-yl)-pyrazolo[1,5-a]pyrimidine as a white solid (90% purity, entry 443) as indicated by 1H-NMR; LC-MS calcd for C26H25N7O2S [M++H]+ 500.18; found 500.2.

Workup

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

Sources & evidence

ORD record
ord-9ad18839608c4b8e90dba0f7879bf49e
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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