Sodium hydride → HCID 49770142, compound

HRID 1157284Notes

Reaction equation

HRID 1157284 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[CH2:40][CH2:41][N:42]1[CH2:47][CH2:46][O:45][CH2:44][CH2:43]1>CN(C=O)C>[F:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:12]=[CH:11][N:10]([CH2:40][CH2:41][N:42]3[CH2:47][CH2:46][O:45][CH2:44][CH2:43]3)[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:31]=[CH:32][CH:33]=[CH:34][CH:35]=5)[N:28]=[N:27][N:26]=4)[CH2:21][CH2:20]3)=[O:18])[C:3]=12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 767274-(2-Chloroethyl)morpholineHCID 178521487HCID 178521487, compound

Product 1

HCID 49770142HCID 49770142, compoundYield 67%

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 mg, 0.8 mmol) and stirred at room temperature for 5 min. 4-(2-chloroethyl)morpholine (149 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 (20 mg, 67%). 1H NMR (500 MHz, MeOD) δ ppm 3.43 (s, 1 H) 3.77 (s, 5 H) 3.81 (s, 5 H) 4.08 (s, 2 H) 4.28 (s, 3 H) 4.37 (s, 4 H) 5.27 (s, 6 H) 7.56 (s, 1 H) 8.06-8.12 (m, 2 H) 8.13 (s, 2 H) 8.38 (s, 1 H) 8.70 (s, 1 H) 8.85 (s, 1 H). LCMS: m/e 600 (M+H)+, ret time 1.22 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-9672433713004d9d9853fa71a83ee23e
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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