Triethylamine → HCID 70032878, compound

HRID 1862040Notes

Reaction equation

HRID 1862040 reaction equation
[NH2:1][C@@H:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([N:13]3[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)[CH:6]=[CH:7][C:8]=2[OH:12])[CH2:3]1.C(N(CC)CC)C.[CH2:27]([O:31][C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1)[CH2:28][CH2:29][CH3:30]>CN(C)C=O>[OH:12][C:8]1[CH:7]=[CH:6][C:5]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[C:4]2[C:9]=1[CH2:10][CH2:11][C@@H:2]([NH:1][C:36](=[O:37])[C:35]1[CH:34]=[CH:33][C:32]([O:31][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:40][CH:39]=1)[CH2:3]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1185614-Butoxybenzoyl chlorideHCID 22082949HCID 22082949, compound

Product 1

HCID 70032878HCID 70032878, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To an ice-cooled solution of (R)-2-amino-5-hydroxy-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (100 mg, 0.38 mmol) and triethylamine (79 μL, 0.57 mmol) in N,N-dimethylformamide (30 mL) was 4-butoxybenzoyl chloride in N,N-dimethylformamide (5 mL) added dropwise. After the addition the reaction was stirred at ambient temperature for 15 min. The solvent was evaporated in vacuo and the residue was purified on a silica gel column using chloroformlmethanol/concentrated ammonium hydroxide (95:5:0.5) as the eluent. Yield: 73 mg (44%) as an amorphous solid: mp 125° C. (decomp.); [α]21D−20° (c=0.25, chloroform); EIMS (70 eV) m/z (relative intensity) 437 (16, M+).

Workup

  1. additionadded dropwise
  2. additionAfter the addition the reaction
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-3db576043651421ab539c25de19c2507
Source dataset
uspto-grants-2003_03
Patent number
US06534652B2

Reaction notes

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