Sodium hydride → HCID 25020157, compound

HRID 2239804Notes

Reaction equation

HRID 2239804 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.CS(O[CH:22]([CH3:42])[CH2:23][N:24]1[C:32]2[N:31]=[C:30]([NH2:33])[N:29]3[N:34]=[C:35]([C:37]4[O:38][CH:39]=[CH:40][CH:41]=4)[N:36]=[C:28]3[C:27]=2[CH:26]=[CH:25]1)(=O)=O>CN(C=O)C>[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[N:11]1[CH2:12][CH2:13][N:14]([CH:22]([CH3:42])[CH2:23][N:24]2[C:32]3[N:31]=[C:30]([NH2:33])[N:29]4[N:34]=[C:35]([C:37]5[O:38][CH:39]=[CH:40][CH:41]=5)[N:36]=[C:28]4[C:27]=3[CH:26]=[CH:25]2)[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27346371-(2,4-Difluorophenyl)piperazineHCID 86623465HCID 86623465, compound

Product 1

HCID 25020157HCID 25020157, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of NaH (13.0 mg, 60 wt % in mineral oil, 0.3 mmol) in 2.0 mL of anhydrous DMF is added 2,4-difluorophenylpiperazine (63 mg, 0.32 mmol). After stirring the solution at RT for 15 min, a solution of 1-(5-amino-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl)propan-2-yl methanesulfonate (80 mg, 0.21 mmol) in 1.5 mL of anhydrous DMF is added. The reaction is stirred at RT under N2 for 12 h. However, very little of product formation is seen by LC/MS. The reaction is then heated at 100° C. for 12 h to complete the reaction as detected by LC/MS. The crude reaction mixture is purified by chromatography to afford 7-(2-(4-(2,4-difluorophenyl)piperazin-1-yl)propyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine: 1H NMR (400 MHz, CD2Cl2) δ 1.05 (d, 3H, J=6.83 Hz), 2.62-272 (m, 2H), 2.83-3.05 (m, 8H), 3.13-3.22 (m, 1H), 4.10 (dd, 1H, J=14.06 Hz and 6.64 Hz), 4.27 (dd, 1H, J=13.96 Hz and 7.52 Hz), 6.61 (dd, 1H, J=3.51 Hz and 1.76 Hz), 6.73 (d, 1H, J=3.51 Hz), 6.76-6.96 (m, 4H), 7.00 (d, 1H, J=3.32 Hz), 7.22 (dd, H, J=3.51 Hz and 0.78 Hz), 7.63 (dd, 1H, J=1.76 HZ and 0.78 Hz).

Workup

  1. stirringThe reaction is stirred at RT under N2 for 12 h
  2. temperatureThe reaction is then heated at 100° C. for 12 h
  3. customthe reaction
  4. customThe crude reaction mixture
  5. customis purified by chromatography

Sources & evidence

ORD record
ord-b5903e6fab8445a9a30d6cc9a55e9f51
Source dataset
uspto-grants-2010_05
Patent number
US07723343B2

Reaction notes

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