1-Acetoxy-2-bromoethane → 6-{2-{2-Hydroxyethyl{2-[4-(2-piperidin-1-ylethoxy)phenyl]ethyl}amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950645Notes

Reaction equation

HRID 1950645 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:18][CH2:17][C:16]3[CH:15]=[C:14]([O:19]C(=O)C(C)(C)C)[CH:13]=[CH:12][C:11]=3[CH2:10]2)=[C:5]([NH:26][C:27](=O)[CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][N:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)=[CH:31][CH:30]=2)[CH:4]=1.[H-].[Na+].[C:47](OCCBr)(=[O:49])[CH3:48].[Cl-].[NH4+]>O1CCCC1>[OH:49][CH2:47][CH2:48][N:26]([CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][N:38]2[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]2)=[CH:31][CH:30]=1)[C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[CH:9]1[CH2:10][CH2:11][C:16]2[CH:15]=[C:14]([OH:19])[CH:13]=[CH:12][C:17]=2[CH2:18]1

Participants

6

Reactant 4

HCID 135641-Acetoxy-2-bromoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 57933831Pivalic acid 6-{4-methoxy-2-{2-[4-(2-piperidin-1-ylethoxy)phenyl]acetylamino}phenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 579341336-{2-{2-Hydroxyethyl{2-[4-(2-piperidin-1-ylethoxy)phenyl]ethyl}amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of pivalic acid 6-{4-methoxy-2-{2-[4-(2-piperidin-1-ylethoxy)phenyl]acetylamino}phenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (30 mg) in tetrahydrofuran (1 ml) was added 60% sodium hydride (2.2 mg), the solution was stirred for 30 minutes at room temperature, then bromoethyl acetate (6.1 μl) was added thereto followed by stirring for 1 hour. To the reaction solution was added a saturated aqueous solution of ammonium chloride, the solution was extracted with chloroform, and concentrated in vacuo. The residue was subjected to the synthetic method of Example 337 described above to provide the title compound (14 mg).

Workup

  1. stirringby stirring for 1 hour
  2. extractionthe solution was extracted with chloroform
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1525b7d3b5842b28739978219944db3
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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