Acetic Acid → HCID 11201075, compound

HRID 545489Notes

Reaction equation

HRID 545489 reaction equation
C(O[C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([CH2:15][NH:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH:13]=[CH:14][C:8]=2[CH:7]=1)=[O:5])C.[C:26]1(=O)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C([O-])(O)=O.[Na+].Cl.[NH2:57][OH:58].C[O-].[Na+]>ClC(Cl)C>[OH:58][NH:57][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([CH2:15][N:16]([CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH:13]=[CH:14][C:8]=2[CH:7]=1)=[O:5]

Participants

9

Reactant 7

HCID 176Acetic AcidHCID 7967CyclohexanoneHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10942334Sodium MethoxideHCID 59556406HCID 59556406, compound

Product 1

HCID 11201075HCID 11201075, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 6-[(4-methoxy-benzylamino)-methyl]-benzo[b]thiophene-2-carboxylic acid ethyl ester (122 mg, 0.34 mmol) and cyclohexanone (46 μL, 0.44 mmol) in anhydrous dichloroethane (5 mL) were added sodium triacetoxyborohydride (216 mg, 1.02 mmol) and acetic acid (20 μL, 0.35 mmol). After the reaction was complete, 5 mL of saturated NaHCO3 was added. The organic layer was separated, washed with 5 mL of water and then concentrated. After drying under high vacuum, the residue was dissolved in anhydrous MeOH (6 mL) and hydroxylamine hydrochloride (90 mg, 1.30 mmol) was added, followed by the addition of NaOMe solution (4.37 M in MeOH, 0.57 mL, 2.5 mmol). The mixture was allowed to stir at rt till the reaction was complete. The reaction mixture was concentrated and the residue was dissolved in a minimal amount of water. The obtained solution was acidified with 2N HCl to pH≈8. The solid formed was filtered, washed with water, collected and purified by flash column chromatography to give 6-{[cyclohexyl-(4-methoxy-benzyl)-amino]-methyl}-benzo[b]thiophene-2-carboxylic acid hydroxyamide as a brownish solid. 1H NMR (DMSO-d6, 200 MHz) δ 11.35 (brs, 1H), 9.23 (brs, 1H), 7.90 (s, 1H), 7.87-7.74 (m, 2H), 7.40 (d, J=8.2 Hz, 1H), 7.23 (d, J=8.8 Hz, 2H), 6.83 (d, J=8.4 Hz, 2H), 3.69 (s, 3H), 3.67 (s, 2H), 3.51 (s, 2H), 2.46-2.24 (m, 1H), 1.92-0.86 (m, 10H). MS (EI): cal'd 425.2 (MH+), exp 425.1 (MH+).

Workup

  1. customThe organic layer was separated
  2. washwashed with 5 mL of water
  3. concentrationconcentrated
  4. customAfter drying under high vacuum
  5. dissolutionthe residue was dissolved in anhydrous MeOH (6 mL)
  6. concentrationThe reaction mixture was concentrated
  7. dissolutionthe residue was dissolved in a minimal amount of water
  8. customThe solid formed
  9. filtrationwas filtered
  10. washwashed with water
  11. customcollected
  12. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-73e2674b6efe4693bc96ddab9e21398e
Source dataset
uspto-grants-2011_05
Patent number
US07935724B2

Reaction notes

Loading…