HCID 11328064, compound → 2-Amino-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (4-diethylamino-phenyl)-amide

HRID 1243135Notes

Reaction equation

HRID 1243135 reaction equation
[CH2:1]([N:3]([CH2:31][CH3:32])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2([NH:23]C(=O)OC(C)(C)C)[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14]2)=[O:12])=[CH:6][CH:5]=1)[CH3:2]>ClCCl.C(O)(C(F)(F)F)=O>[CH2:31]([N:3]([CH2:1][CH3:2])[C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([C:13]2([NH2:23])[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14]2)=[O:12])=[CH:8][CH:9]=1)[CH3:32]

Participants

4

Reactant 1

HCID 11328064HCID 11328064, compound

Product 1

HCID 865961192-Amino-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid (4-diethylamino-phenyl)-amideYield 97.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

(2-(4-Diethylamino-phenylcarbamoyl)-1,2,3,4-tetrahydro-naphthalen-2-yl)-carbamic acid tert-butyl ester from Example 3 (320 mg) was dissolved in dichloromethane (10 mL) and TFA (5.0 mL). The volatiles were removed after 2 h. The amine-TFA salt was then dissolved in ethyl acetate (30 mL) and washed with 1 N NaOH. The organic phase was dried over MgSO4 and purified by column chromatography to provide the titled compound (240 mg, 97%).

Workup

  1. customThe volatiles were removed after 2 h
  2. dissolutionThe amine-TFA salt was then dissolved in ethyl acetate (30 mL)
  3. washwashed with 1 N NaOH
  4. dry with materialThe organic phase was dried over MgSO4
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-c987384c6a9648e3ad207e07103e7d44
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

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