Sodium Hydroxide → HCID 86623816, compound

HRID 251228Notes

Reaction equation

HRID 251228 reaction equation
[CH3:1][C:2]1[C:3]([N:9]([CH:16]2[C:25]3[N:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:19][CH2:18][CH2:17]2)[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][OH:15])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[O-:26][C:27]#[N:28].[Na+].[OH-].[Na+]>O>[CH3:1][C:2]1[C:3]([N:9]([CH:16]2[C:25]3[N:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:19][CH2:18][CH2:17]2)[CH2:10][CH2:11][CH2:12][CH2:13][N:14]([OH:15])[C:27]([NH2:28])=[O:26])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 517096Sodium CyanateHCID 86623817HCID 86623817, compound

Product 1

HCID 86623816HCID 86623816, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-{4-[(3,5-Dimethyl-pyridin-2-yl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-hydroxylamine (HBr salt) (180 mg, 0.25 mmol) was dissolved in H2O (2.5 mL) and treated with sodium cyanate (65 mg, 1.0 mmol) for 2 hours. 15% aqueous NaOH solution (0.1 mL) was added and the aqueous was extracted with CH2Cl2 (3×5 mL). The combined organics were then dried (Na2SO4) and concentrated under reduced pressure to afford, after radial chromatographic purification on a silica gel plate (3% NH4OH/CH3CN) N-{4-[(3,5-dimethyl-pyridin-2-yl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-N-hydroxyurea (73 mg, 73%).

Workup

  1. extractionthe aqueous was extracted with CH2Cl2 (3×5 mL)
  2. dry with materialThe combined organics were then dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customto afford
  5. customafter radial chromatographic purification on a silica gel plate (3% NH4OH/CH3CN) N-{4-[(3,5-dimethyl-pyridin-2-yl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-N-hydroxyurea (73 mg, 73%)

Sources & evidence

ORD record
ord-0f29edb7c0e54be39a37987fcd15aa68
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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