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

HRID 1713126Notes

Reaction equation

HRID 1713126 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:10]1[CH:19]=[CH:18][C:17]2[CH2:16][N:15]([CH2:20][C:21]([N:23]3[CH2:28][CH2:27][N:26]([CH:29]4[CH2:32][CH2:31][CH2:30]4)[CH2:25][CH2:24]3)=[O:22])[CH2:14][CH2:13][C:12]=2[N:11]=1>CN(C=O)C>[CH:1]1([O:6][C:10]2[CH:19]=[CH:18][C:17]3[CH2:16][N:15]([CH2:20][C:21]([N:23]4[CH2:24][CH2:25][N:26]([CH:29]5[CH2:32][CH2:31][CH2:30]5)[CH2:27][CH2:28]4)=[O:22])[CH2:14][CH2:13][C:12]=3[N:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7298CyclopentanolHCID 24758Sodium hydrideHCID 574205742-Chloro-6-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-5,6,7,8-tetrahydro-1,6-naphthyridine

Product 1

HCID 574205772-Cyclopentyloxy-6-[2-(4-Cyclobutylpiperazin-1-Yl)-2-Oxoethyl]-5,6,7,8-Tetrahydro-1,6-Naphthyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of cyclopentanol (99 mg, 1.15 mmol) in DMF (5 mL) is added NaH (60% in mineral oil, 18.4 mg, 0.46 mmol), and the mixture is stirred at rt for 30 min. 2-Chloro-6-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-5,6,7,8-tetrahydro-1,6-naphthyridine (80 mg, 0.23 mmol) is added and the mixture is heated at 100° C. for 2 hr. Solvent is removed and the residue is partitioned between water (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): 399.3; 1H NMR (δ, CDCl3): 7.17 (d, 1H), 6.46 (d, 1H), 5.28 (m, 1H), 3.64 (q, 4H), 3.58 (s, 2H), 3.36 (s, 2H), 2.80-2.88 (m, 4H), 2.63-2.73 (m, 1H), 2.28 (q, 4H), 1.58-2.08 (m, 14H).

Workup

  1. temperaturethe mixture is heated at 100° C. for 2 hr
  2. customSolvent is removed
  3. customthe residue is partitioned between water (10 mL) and DCM (10 mL)
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted with DCM (10 ml)
  6. customThe combined extracts are dried
  7. customevaporated
  8. customThe residue is purified by PTLC

Sources & evidence

ORD record
ord-a529f7b9afbf43cfb5c9d8c0ccffc446
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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