1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178480888, compound

HRID 222017Notes

Reaction equation

HRID 222017 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][C:15]4[C:21]5[C:22]([O:26]CCC6C=CC([N+]([O-])=O)=CC=6)=[N:23][CH:24]=[N:25][C:20]=5[S:19][C:16]=43)=[N:11]2)[CH2:4][CH2:3]1.C1CCN2C(=NCCC2)CC1>N1C=CC=CC=1>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][C:15]4[C:21]5=[C:22]([OH:26])[N:23]=[CH:24][N:25]=[C:20]5[S:19][C:16]=43)=[N:11]2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58346558HCID 58346558, compound

Product 1

HCID 178480888HCID 178480888, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-[2-(4-methylpiperazin-1-yl)ethyl]-6-[2-(4-nitrophenyl)ethoxy]-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazole (4.12 g, 7.93 mmol) in pyridine (100 mL) was added DBU (4.83 g, 31.72 mmol) and the resulting reaction mixture was stirred at room temperature overnight. Analytical HPLC showed no more starting material present and two new peaks appeared. Solvents were evaporated and the residue was dissolved in water and CH2Cl2. pH of the aqueous layer was adjusted to about 7. The organic phase contains the N-alkylated side product and no desired product. The desired product is in the aqueous phase. After separation of the layers, the pH of the aqueous was further adjusted to about 10 and it was concentrated to dryness. The resulting solid was washed with MeOH, then small amount of water, and air dried to afford a light yellow solid (0.79 g, 27%) as the desired product. The MeOH filtrates were concentrated to give a yellow solid, which was washed with EtOAc, air-dried to give another batch of desired product (1.5 g, 36%) as a light yellow solid. 1H-NMR (D2O) δ 7.82 (s, 1H), 7.56 (s, 1H), 4.26 (t, 2H), 3.30 (broad, 4 h), 3.21 (t, 2H), 3.07 (broad, 4H), 2.99 (t, 2H), 2.78 (s, 3H), 2.67 (t, 2H); LCMS RT=0.30 min; [M+H]+=371.3.

Workup

  1. customthe resulting reaction mixture
  2. customSolvents were evaporated
  3. dissolutionthe residue was dissolved in water
  4. customAfter separation of the layers
  5. concentrationwas concentrated to dryness
  6. washThe resulting solid was washed with MeOH
  7. dry with materialsmall amount of water, and air dried

Sources & evidence

ORD record
ord-f4716283105f4da387c5049715b82a82
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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