Sodium hydride → HCID 22171087, compound

HRID 2376242Notes

Reaction equation

HRID 2376242 reaction equation
[H-].[Na+].[N:3]1[NH:4][C:5]([SH:8])=[N:6][CH:7]=1.Br[CH2:10][CH:11]([C:34]1[CH:35]=[C:36]([CH3:40])[CH:37]=[CH:38][CH:39]=1)[CH2:12][C:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[N:15]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[N:14]=1>CN(C)C=O>[Cl:25][C:20]1[CH:19]=[C:18]([C:16]2[N:15]([C:26]3[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=3)[N:14]=[C:13]([CH2:12][CH:11]([C:34]3[CH:35]=[C:36]([CH3:40])[CH:37]=[CH:38][CH:39]=3)[CH2:10][S:8][C:5]3[NH:4][N:3]=[CH:7][N:6]=3)[CH:17]=2)[CH:23]=[CH:22][C:21]=1[Cl:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 22171084HCID 22171084, compoundHCID 178527896HCID 178527896, compound

Product 1

HCID 22171087HCID 22171087, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (4.0 mg, 60% dispersion in oil) in N,N-dimethylformamide (1.0 mL) at 0° C. was added a solution of 2H-[1,2,4]triazole-3-thiol (10.0 mg, 0.1 mmol, 1.1 equiv) in N,N-dimethylformamide (1.0 mL). The mixture was stirred at 0° C. for 30 min then a solution of 3-(3-bromo-2-m-tolyl-propyl)-5-(3,4-dichloro-phenyl)-1-(4-methoxy-phenyl)-1H-pyrazole (48 mg, 0.09 mmol, 1.0 equiv) in N,N-dimethylformamide (1.0 mL) was added. The reaction mixture was brought to room temperature then was stirred for 2 h. The reaction was quenched with satd aq ammonium chloride (1.0 mL), and the resulting mixture was diluted with water (10.0 mL), and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with water (10 mL) then brine (10 mL), dried (Na2SO4), and concentrated under reduced pressure. The crude residue was purified by reversed-phase HPLC to yield the title compound (39 mg, 80%). HPLC: Rt=3.26 (Method B). MS (ESI): mass calculated for C28H25Cl2N5OS, 549.12; m/z found, 550.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 8.32 (br s, 1H), 7.50 (d, J=8.4 Hz, 1H), 7.35 (d, J=2.1 Hz, 1H), 7.07-7.04 (m, 5H), 6.95 (dd, J=8.4, 21. HZ, 2H), 6.89 (d, J=9.0 Hz, 2H), 6.31 (s, 1H), 3.70 (s, 3H), 3.48 (dd, J=12.9, 6.3 Hz, 1H), 3.36 (dd, J=12.7, 8.2 Hz, 1H), 3.26 (m, 1H), 3.07 (dd, J=14.9, 6.4 Hz, 1H), 2.91 (dd, J=14.9, 8.2 Hz, 1H), 2.21 (s, 3H).

Workup

  1. customwas brought to room temperature
  2. stirringthen was stirred for 2 h
  3. customThe reaction was quenched with satd aq ammonium chloride (1.0 mL)
  4. additionthe resulting mixture was diluted with water (10.0 mL)
  5. extractionextracted with ethyl acetate (3×10 mL)
  6. washThe combined organic layers were washed with water (10 mL)
  7. dry with materialbrine (10 mL), dried (Na2SO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe crude residue was purified by reversed-phase HPLC

Sources & evidence

ORD record
ord-a91acef09f614f6797c9153f760d4a14
Source dataset
uspto-grants-2008_12
Patent number
US07465808B2

Reaction notes

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