Lithium Hydroxide → HCID 22506220, compound

HRID 1814428Notes

Reaction equation

HRID 1814428 reaction equation
O.[OH-].[Li+].C([O:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:23][CH2:24][CH2:25][NH:26][C:27]([NH:29][C:30]1[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][CH:31]=1)=[O:28])[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1)(=O)C.[OH-].[Li+].CO.C(Cl)(Cl)Cl>O.CO>[Br:36][C:33]1[CH:34]=[CH:35][C:30]([NH:29][C:27](=[O:28])[NH:26][CH2:25][CH2:24][CH2:23][N:12]([CH:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][CH2:14]2)[CH2:11][CH2:10][CH2:9][CH2:8][OH:7])=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 168937Lithium hydroxide, monohydrateHCID 21584188Chloroform methanolHCID 22506166HCID 22506166, compound

Product 1

HCID 22506220HCID 22506220, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Lithium hydroxide monohydrate (11 mg, 0.26 mmol) was added to a solution of 4-[[3-(4-bromophenylureido)propyl](1,2,3,4-tetrahydro-1-naphthyl)amino]butyl acetate (67 mg, 0.13 mmol) in 10% water/methanol (1.1 ml). After stirring at RT for 16 h, additional lithium hydroxide monohydrete (22 mg, 0.52 mmol) was added. The reaction mixture was stirred at RT for 17 h, and then concentrated under vacuum to dryness. The residue was adsorbed on a plate of silica get and then developed with 10% methanol/chloroform to afford 4-[[3-(4-bromophenylureido)propyl](1,2,3,4-tetrahydro-1-naphthyl)amino]-1-butanol (48 mg, 77%): MS(ES+) m/e 476 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 8.52 (br, 1H), 7.63 (d, J=7.6 Hz, 1H), 7.36 (m, 4H), 7.11-7.03 (m, 3H), 6.10 (br, 1H), 4.33 (br, 1H), 3.90 (m, 1H), 3.37 (m, 2H), 3.13 (m, 1H), 3.02 (m, 1H), 2.67 (m, 2H), 2.54-2.47 (m, 4H), 1.93 (m, 2H), 1.58 (m, 4H), 1.44 (m, 4H).

Workup

  1. stirringThe reaction mixture was stirred at RT for 17 h
  2. concentrationconcentrated under vacuum to dryness
  3. customget

Sources & evidence

ORD record
ord-a669eac5e38e44c4969a5a30f2f308a5
Source dataset
uspto-grants-2005_04
Patent number
US06875884B1

Reaction notes

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