Water → Ethyl 1-(2,4-dimethoxybenzyl)-7-(2-hydroxymethylpiperidin-1-yl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylate

HRID 1867937Notes

Reaction equation

HRID 1867937 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:28])[C:7]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:8][N:9]2[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[O:21][CH3:22])=[CH:4][C:3]=1F.N1([CH2:36][OH:37])CCCCC1.[CH:38](N(C(C)C)CC)([CH3:40])[CH3:39].O.[C:48](#[N:50])[CH3:49]>>[CH3:22][O:21][C:14]1[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=1[CH2:12][N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([N:50]3[CH2:40][CH2:38][CH2:39][CH2:49][CH:48]3[CH2:36][OH:37])[N:11]=2)[C:6](=[O:28])[C:7]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:8]1

Participants

6

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 446909Piperidin-1-ylmethanolHCID 13937202Ethyl 7-chloro-1-(2,4-dimethoxybenzyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Product 1

HCID 69030307Ethyl 1-(2,4-dimethoxybenzyl)-7-(2-hydroxymethylpiperidin-1-yl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylate

Conditions

Temperature
75 °C

Procedure

A mixture of EXAMPLE 1B (2.15 g), piperidinylmethanol (890 mg) and diisopropylethylamine (2.5 mL) in acetonitrile (50 mL) at 25° C. was stirred for 24 hours, heated at 75° C. for 5 days, cooled, treated with water, and extracted with dichloromethane (200 mL). The extract was washed with water and 1M hydrochloric acid and concentrated.

Workup

  1. temperaturecooled
  2. extractionextracted with dichloromethane (200 mL)
  3. washThe extract was washed with water and 1M hydrochloric acid
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-be7ac9be88d94205aa7e39f7e88acfe6
Source dataset
uspto-grants-2009_12
Patent number
US07632946B2

Reaction notes

Loading…