Sodium Hydroxide → HCID 86623814, compound

HRID 251226Notes

Reaction equation

HRID 251226 reaction equation
[CH3:1][C:2]1[C:3]([N:9]([CH:15]2[C:24]3[N:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH2:18][CH2:17][CH2:16]2)[CH2:10][CH2:11][CH2:12][NH:13][OH:14])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[O-:25][C:26]#[N:27].[Na+].[OH-].[Na+]>O>[CH3:1][C:2]1[C:3]([N:9]([CH:15]2[C:24]3[N:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH2:18][CH2:17][CH2:16]2)[CH2:10][CH2:11][CH2:12][N:13]([OH:14])[C:26]([NH2:27])=[O:25])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 517096Sodium CyanateHCID 86623815HCID 86623815, compound

Product 1

HCID 86623814HCID 86623814, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-{3-[(3,5-Dimethyl-pyridin-2-yl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-propyl}-hydroxylamine (HBr salt) (138 mg, 0.22 mmol) was dissolved in H2O (2 mL) and treated with sodium cyanate (42 mg, 0.65 mmol) for 3.5 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-{3-[(3,5-dimethyl-pyridin-2-yl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-propyl}-N-hydroxyurea (42 mg, 50%).

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-{3-[(3,5-dimethyl-pyridin-2-yl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-propyl}-N-hydroxyurea (42 mg, 50%)

Sources & evidence

ORD record
ord-3ba2db1bbc814386a339d541bfd1f84a
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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