Sodium hydride → HCID 49770140, compound

HRID 1157283Notes

Reaction equation

HRID 1157283 reaction equation
[F:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:12]=[CH:11][NH:10][N:9]=2)=[C:4]2[NH:13][CH:14]=[C:15]([C:16](=[O:36])[C:17]([N:19]3[CH2:24][CH2:23][N:22]([C:25]4[N:29]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[N:28]=[N:27][N:26]=4)[CH2:21][CH2:20]3)=[O:18])[C:3]=12.[H-].[Na+].Cl.Cl[CH2:41][CH2:42][N:43]([CH3:45])[CH3:44]>CN(C=O)C>[CH3:44][N:43]([CH3:45])[CH2:42][CH2:41][N:10]1[CH:11]=[CH:12][C:8]([C:5]2[N:6]=[CH:7][C:2]([F:1])=[C:3]3[C:15]([C:16](=[O:36])[C:17]([N:19]4[CH2:24][CH2:23][N:22]([C:25]5[N:29]([C:30]6[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=6)[N:28]=[N:27][N:26]=5)[CH2:21][CH2:20]4)=[O:18])=[CH:14][NH:13][C:4]=23)=[N:9]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 178521487HCID 178521487, compound

Product 1

HCID 49770140HCID 49770140, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(4-fluoro-7-(1H-pyrazol-3-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-phenyl-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione (40 mg, 0.08 mmol) in DMF (1 mL) was treated with sodium hydride (60% in oil, 33.0 mg, 0.8 mmol) and stirred at room temperature for 5 min. 2-chloro-N,N-dimethylethanamine hydrochloride (115.2 mg, 0.8 mmol) was added and the mixture was stirred at rt for 1 h. Reaction was quenched with H2O and concentrated under reduced pressure. The residue was dissolved in DMF and purified using reverse phase prep HPLC to afford the title compound as a white solid (15 mg, 34%). 1H NMR (500 MHz, MeOD) δ ppm 2.96 (s, 6 H) 3.37 (s, 2 H) 3.63 (s, 2 H) 3.82 (s, 2 H) 3.89 (s, 2 H) 4.76 (s, 2 H) 7.11 (s, 1 H) 7.59 (s, 1 H) 7.64 (s, 2 H) 7.68 (s, 2 H) 7.92 (s, 1 H) 8.25 (s, 1 H) 8.36 (s, 1 H). LCMS: m/e 558 (M+H)+, ret time 1.37 min (method 3).

Workup

  1. stirringthe mixture was stirred at rt for 1 h
  2. customReaction
  3. customwas quenched with H2O
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in DMF
  6. custompurified

Sources & evidence

ORD record
ord-95934af3115a42c48ff73d007bc92910
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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