Potassium Carbonate → 6-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one

HRID 1713120Notes

Reaction equation

HRID 1713120 reaction equation
[NH:1]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]1=[O:11].Cl[CH2:13][C:14]([N:16]1[CH2:21][CH2:20][N:19]([CH:22]2[CH2:25][CH2:24][CH2:23]2)[CH2:18][CH2:17]1)=[O:15].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH:22]1([N:19]2[CH2:20][CH2:21][N:16]([C:14](=[O:15])[CH2:13][N:7]3[CH2:8][CH2:9][C:10]4[NH:1][C:2](=[O:11])[CH:3]=[CH:4][C:5]=4[CH2:6]3)[CH2:17][CH2:18]2)[CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 210711895,6,7,8-Tetrahydro-1,6-naphthyridin-2(1H)-oneHCID 574205621-(Chloroacetyl)-4-cyclobutylpiperazine

Product 1

HCID 574206516-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one (98 mg, 0.653 mmol), 1-(chloroacetyl)-4-cyclobutylpiperazine (142 mg, 0.653 mmol), K2CO3 (360 mg, 2.61 mmol) and KI (12 mg, 0.07 mmol) in CH3CN (15 mL) is stirred at rt overnight. The solvent is removed in vacuo and the residue is partitioned between water (10 mL) and EtOAc (20 mL). The layers are separated and the aqueous layer is extracted with EtOAc (2×10 mL) and the combined extracts are dried and evaporated. The resulting oil is purified by PTLC with DCM/MeOH/NH4OH (100:5:0.5) to give the title compound as a light yellow solid. MS (M+1): 331.2; 1H NMR (δ, CDCl3): 7.13 (d, 1H0, 6.38 (d, 1H), 3.60 (q, 4H), 3.44 (s, 2H), 3.35 (s, 2H), 2.79 (s, 2H), 2.63-2.75 (m, 1H), 2.26 (q, 4H), 1.63-2.06 (m, 6H).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between water (10 mL) and EtOAc (20 mL)
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (2×10 mL)
  5. customthe combined extracts are dried
  6. customevaporated
  7. customThe resulting oil is purified by PTLC with DCM/MeOH/NH4OH (100:5:0.5)

Sources & evidence

ORD record
ord-3c050de42b0a473cb88e65134c508eca
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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