Diisopropylethylamine → HCID 24950070, compound

HRID 1784364Notes

Reaction equation

HRID 1784364 reaction equation
[F:1][C:2]1[CH:7]=[N:6][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[N:9]2)=[C:4]2[NH:13][CH:14]=[C:15]([C:16](=[O:20])[C:17]([OH:19])=O)[C:3]=12.[C:21]1([C:27]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)=[C:28]([C:31]#[N:32])[C:29]#[N:30])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(OP(ON1C(=O)C2C=CC=CC=2N=N1)(OCC)=O)C.CCN(C(C)C)C(C)C>CN(C=O)C>[F:1][C:2]1[CH:7]=[N:6][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[N:9]2)=[C:4]2[NH:13][CH:14]=[C:15]([C:16](=[O:20])[C:17]([N:36]3[CH2:35][CH2:34][N:33]([C:27]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[C:28]([C:31]#[N:32])[C:29]#[N:30])[CH2:38][CH2:37]3)=[O:19])[C:3]=12

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 42939953-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-oneHCID 58806128HCID 58806128, compoundHCID 86616769HCID 86616769, compound

Product 1

HCID 24950070HCID 24950070, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-fluoro-7-(1H-1,2,3-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid (70 mg), 2-(phenyl(piperazin-1-yl)methylene)malononitrile (55 mg), 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT) (200 mg) and Hunig's Base (0.1 ml) were combined in 1.5 ml of DMF. The mixture was stirred at room temperature for 16 hours. Then, DMF was removed via evaporation at reduced pressure and the residue was partitioned between ethyl acetate (10 ml) and water (10 ml). The organic layer washed saturated NaHCO3 solution (3×100 ml), and brine (10 ml). The organic phase was dried over anhydrous MgSO4-Concentration in vacuo provided a crude product, which was purified using Shimadzu automated preparative HPLC System to afford 2-((4-(2-(4-fluoro-7-(1H-1,2,3-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetyl)piperazin-1-yl)(phenyl)methylene)malononitrile.

Workup

  1. customThen, DMF was removed via evaporation at reduced pressure
  2. customthe residue was partitioned between ethyl acetate (10 ml) and water (10 ml)
  3. washThe organic layer washed saturated NaHCO3 solution (3×100 ml), and brine (10 ml)
  4. dry with materialThe organic phase was dried over anhydrous MgSO4-Concentration in vacuo
  5. customprovided a crude product, which
  6. customwas purified

Sources & evidence

ORD record
ord-211a85b0eae84c81bc28ab31d4d18887
Source dataset
uspto-grants-2009_03
Patent number
US07504399B2

Reaction notes

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