Ammonia → pivalic acid (R)-6-{2-{ethyl[4-(piperidin-4-yloxy)benzyl]amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

HRID 1950202Notes

Reaction equation

HRID 1950202 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(OC(N1CCC(OC2C=CC(CNCC[C:47]3[CH:52]=[C:51]([O:53][CH3:54])[CH:50]=[CH:49][C:48]=3[C@@H:55]3[CH2:64][CH2:63][C:62]4[C:57](=[CH:58][CH:59]=[C:60]([O:65][C:66](=[O:71])[C:67]([CH3:70])([CH3:69])[CH3:68])[CH:61]=4)[CH2:56]3)=CC=2)CC1)=O)(C)(C)C.F[C:73](F)(F)[C:74](O)=O.[NH3:79]>ClCCl>[CH2:73]([N:79]([CH2:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[CH:20][CH:19]=1)[C:47]1[CH:52]=[C:51]([O:53][CH3:54])[CH:50]=[CH:49][C:48]=1[C@@H:55]1[CH2:64][CH2:63][C:62]2[CH:61]=[C:60]([O:65][C:66](=[O:71])[C:67]([CH3:68])([CH3:69])[CH3:70])[CH:59]=[CH:58][C:57]=2[CH2:56]1)[CH3:74]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 22632605tert-Butyl 4-(4-formylphenoxy)piperidine-1-carboxylateHCID 66625512(R)-4-{4-{{{2-[6-(2,2-dimethylpropionyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-5-methoxyphenyl}ethylamino}methyl}phenoxy}piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 66626417pivalic acid (R)-6-{2-{ethyl[4-(piperidin-4-yloxy)benzyl]amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Synthesized from (R)-6-(2-ethylamino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (20 mg) and 4-(4-formylphenoxy)piperidine-1-carboxylic acid tert-butyl ester (72 mg) according to an analogous synthetic method to Example 212, to a solution of the resulting (R)-4-{4-{{{2-[6-(2,2-dimethylpropionyloxy)-1,2,3,4-tetrahydronaphthalen-2-yl]-5-methoxyphenyl}ethylamino}methyl}phenoxy}piperidine-1-carboxylic acid tert-butyl ester crude product in dichloromethane (0.5 ml) was added trifluoroacetic acid (0.5 ml), the solution was let to stand for 30 minutes at room temperature, then neutralized with ammonia solution, extracted with chloroform, then concentrated under a nitrogen stream to give pivalic acid (R)-6-{2-{ethyl[4-(piperidin-4-yloxy)benzyl]amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester. Synthesized from the total amount of the resulting crude product according to an analogous synthetic method to Example 213 and purified by LC-MS, the title compound (5.0 mg) was obtained.

Workup

  1. extractionextracted with chloroform
  2. concentrationconcentrated under a nitrogen stream

Sources & evidence

ORD record
ord-b68753234a12449a896b7a3b904c5217
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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