Dimethylformamide → HCID 178492071, compound

HRID 2376220Notes

Reaction equation

HRID 2376220 reaction equation
COC1C=CC([C:9]2(C)[CH:14]=[CH:13][C:12]([N:15]3[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([C:24]4[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=4)[C:22]#[N:23])=[N:16]3)=[CH:11][CH2:10]2)=CC=1.[N-:32]=[N+:33]=[N-:34].[Na+].[Cl-].[NH4+].CN([CH:41]=[O:42])C>O>[CH3:41][O:42][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:19]([C:27]3[CH:26]=[CH:25][C:24]([CH3:21])=[CH:29][CH:28]=3)=[CH:18][C:17]([CH2:20][CH:21]([C:22]3[NH:23][N:34]=[N:33][N:32]=3)[C:24]3[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=3)=[N:16]2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 69196950HCID 69196950, compound

Product 1

HCID 178492071HCID 178492071, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

3-[1-(4-Methoxy-phenyl)-p-tolyl-1H-pyrazol-3-yl]-2-m-tolyl-propionitrile (Example 73, 0.10 g, 0.24 mmol), sodium azide (32 mg, 0.50 mmol) and ammonium chloride (26 mg, 0.50 mmol) were mixed in DMF (3.0 mL) and heated at 100° C. for 4 days. The reaction mixture was cooled, diluted with water (25 mL) and extracted with EtOAc (3×25 mL). The combined organic layers were washed with brine (1×25 mL) and dried with Na2SO4, and the solvent was removed under reduced pressure yielding 21 mg (20%) of 5-{2-[1-(4-methoxy-phenyl)-5-p-tolyl-1H-pyrazol-3-yl]-1-m-tolyl-ethyl}-1H-tetrazole. HPLC: Rt=3.16 (Method B). MS (ES+): mass calculated for C27H26N6O, 450.22; m/z found 451.2 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 7.25-7.17 (m, 3H), 7.12 (d, J=7.9 Hz, 2H), 7.07 (d, J=7.4 Hz, 1H), 7.04 (d, J=9.0 Hz, 2H), 6.99(d, J=8.1 Hz, 2H), 6.92 (d, J=9.0 Hz, 2H), 6.23 (s, 1H), 4.85 (dd, J=6.7, 9.2 Hz, 1H), 3.75 (s, 3H), 3.60 (dd, J=9.3, 14.8 Hz, 1H), 3.34 (dd, J=6.4, 14.4 Hz, 1H), 2.28 (s, 3H), 2.26 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with EtOAc (3×25 mL)
  3. washThe combined organic layers were washed with brine (1×25 mL)
  4. dry with materialdried with Na2SO4
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b989a0f1dd214b1b965f16fa08fe1228
Source dataset
uspto-grants-2008_12
Patent number
US07465808B2

Reaction notes

Loading…