Acetic Acid → HCID 57467344, compound

HRID 510550Notes

Reaction equation

HRID 510550 reaction equation
[NH2:1][CH:2]1[CH:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:10]2[CH:9]=[C:8]([CH2:20][CH2:21][CH2:22][NH:23][S:24]([CH2:27][CH:28]3[CH2:30][CH2:29]3)(=[O:26])=[O:25])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[C:31](O)(=O)[CH3:32].[CH:35](=O)[CH3:36].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[ClH:19].[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][CH:11]2[C:10]3[CH:9]=[C:8]([CH2:20][CH2:21][CH2:22][NH:23][S:24]([CH2:27][CH:28]4[CH2:29][CH2:30]4)(=[O:26])=[O:25])[CH:7]=[CH:6][C:5]=3[CH2:4][CH2:3][CH:2]2[N:1]([CH2:31][CH3:32])[CH2:35][CH3:36])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 57467313HCID 57467313, compound

Product 1

HCID 57467344HCID 57467344, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

N-(3-(7-Amino-8-(4-chlorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl)propyl)-1-cyclopropylmethanesulfonamide (49 mg, 0.11 mmol) was dissolved in dichloromethane (2 mL). Acetic acid (7 μL, 0.11 mmol) was added followed by acetaldehyde (18 μL, 0.322 mmol) in dichloromethane (2 mL) and sodium triacetoxyborohydride (34 mg, 0.16 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with dichloromethane (20 mL) and washed with water (2×10 mL). The organic layer was dried (MgSO4) and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography (silica gel, dichloromethane, methanol). The amine was dissolved in dichloromethane (3 mL) and excess hydrochloric acid in ethanol was added. The solvents were evaporated and the product dried in vacuo. Yield: 22 mg (0.041 mmol, 38%).

Workup

  1. washwashed with water (2×10 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent was evaporated in vacuo
  4. customThe crude product was purified by flash chromatography (silica gel, dichloromethane, methanol)
  5. dissolutionThe amine was dissolved in dichloromethane (3 mL)
  6. additionexcess hydrochloric acid in ethanol was added
  7. customThe solvents were evaporated
  8. customthe product dried in vacuo

Sources & evidence

ORD record
ord-dabeeeb646194efa9dd9d89f56632142
Source dataset
uspto-grants-2015_08
Patent number
US09096619B2

Reaction notes

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