Water → HCID 59416006, compound

HRID 2061883Notes

Reaction equation

HRID 2061883 reaction equation
Cl.[I:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH:14]1[CH2:18][CH2:17][NH:16][CH2:15]1)[CH:8]=[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:6]2=[O:24].Cl.O.[N:27]1([CH2:33][CH:34]=O)[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C([BH3-])#N.[Na+].O>CO>[I:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH:14]1[CH2:18][CH2:17][N:16]([CH2:34][CH2:33][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH2:15]1)[CH:8]=[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:6]2=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 17998884Morpholin-4-yl-acetaldehyde monohydrate hydrochlorideHCID 68470833HCID 68470833, compound2×

Product 1

HCID 59416006HCID 59416006, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

Ethyl 6-iodo-4-oxo-1-(pyrrolidin-3-ylmethyl)-1,4-dihydroquinoline-3-carboxylate hydrochloride (Intermediate 127, 500 mg, 1.08 mmol) was suspended in methanol (15 mL) then morpholine-4-ylacetaldehyde monohydrate hydrochloride (1 g, 5.4 mmol) and sodium cyanoborohydride (612 mg, 9.7 mmol) were added. The reaction was stirred at 23° C. for 16 h. The volume of the reaction was reduced by half and water (25 mL) was added. The suspension was extracted with 2:1 ethyl acetate: tetrahydrofuran (3×10 mL). The organic phases were combined, dried over sodium sulfate, and the solvent was removed in vacuo. The residue was passed through a plug of silica gel (2 g) eluting with 10% methanol in dichloromethane to remove any remaining borohydride. The solid was then dried in a vacuum oven at 50° C. for 18 h to give 225 mg (38% yield) of ethyl 6-iodo-1-((1-(2-morpholinoethyl)pyrrolidin-3-yl)methyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate as an off white solid.

Workup

  1. additionwas added
  2. extractionThe suspension was extracted with 2:1 ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed in vacuo
  5. washeluting with 10% methanol in dichloromethane
  6. customto remove any remaining borohydride
  7. customThe solid was then dried in a vacuum oven at 50° C. for 18 h

Sources & evidence

ORD record
ord-1c479a1d460e4ee2a99d1501a55bb819
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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