Pyrrolidine → 6-[2-(4-Cyclobutylpiperazin-1-Yl)-2-Oxoethyl]-2-Pyrrolidin-1-Yl-5,6,7,8-Tetrahydro-1,6-Naphthyridine

HRID 1713125Notes

Reaction equation

HRID 1713125 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[CH2:8][N:7]([CH2:12][C:13]([N:15]3[CH2:20][CH2:19][N:18]([CH:21]4[CH2:24][CH2:23][CH2:22]4)[CH2:17][CH2:16]3)=[O:14])[CH2:6][CH2:5][C:4]=2[N:3]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>>[CH:21]1([N:18]2[CH2:19][CH2:20][N:15]([C:13](=[O:14])[CH2:12][N:7]3[CH2:6][CH2:5][C:4]4[N:3]=[C:2]([N:25]5[CH2:29][CH2:28][CH2:27][CH2:26]5)[CH:11]=[CH:10][C:9]=4[CH2:8]3)[CH2:16][CH2:17]2)[CH2:24][CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 574205742-Chloro-6-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-5,6,7,8-tetrahydro-1,6-naphthyridine

Product 1

HCID 574205766-[2-(4-Cyclobutylpiperazin-1-Yl)-2-Oxoethyl]-2-Pyrrolidin-1-Yl-5,6,7,8-Tetrahydro-1,6-Naphthyridine

Conditions

Temperature
170 °C

Procedure

A mixture of 2-chloro-6-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-5,6,7,8-tetrahydro-1,6-naphthyridine (80 mg, 0.23 mmol) and pyrrolidine (2.5 mL) is heated by microwave (300 w) at 170° C. for 2 hr. Solvent is removed and the residue is partitioned between saturated NaHCO3 solution (10 mL) and DCM (10 mL). The layers are separated and the aqueous layer is extracted with DCM (10 ml). The combined extracts are dried and evaporated. The residue is purified by PTLC to give the title compound as a light yellow oil. MS (M+1): 384.3; 1H NMR (5, CDCl3): 7.07 (d, 1H), 6.16 (d, 1H), 3.62-3.69 (m, 4H), 3.53 (s, 2H), 3.40-3.44 (m, 4H), 3.34 (s, 2H), 2.78-2.90 (m, 4H), 2.61-2.72 (m, 1H), 2.27 (q, 4H), 1.63-2.04 (m, 10H).

Workup

  1. customSolvent is removed
  2. customthe residue is partitioned between saturated NaHCO3 solution (10 mL) and DCM (10 mL)
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with DCM (10 ml)
  5. customThe combined extracts are dried
  6. customevaporated
  7. customThe residue is purified by PTLC

Sources & evidence

ORD record
ord-aa227cd084264a8fa7a485e9a764401f
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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