pivalic acid (R)-6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester → (R)-6-{2-{[4-(2-Amino-2-methylpropoxy)-3-fluorobenzyl]ethylamino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 2423800Notes

Reaction equation

HRID 2423800 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[C@@H:14]1[CH2:23][CH2:22][C:21]2[CH:20]=[C:19]([O:24]C(=O)C(C)(C)C)[CH:18]=[CH:17][C:16]=2[CH2:15]1)[CH3:2].[F:31][C:32]1[CH:50]=[C:49]([CH:51]=O)[CH:48]=[CH:47][C:33]=1[O:34][CH2:35][C:36]([NH:39]C(=O)OC(C)(C)C)([CH3:38])[CH3:37]>>[NH2:39][C:36]([CH3:38])([CH3:37])[CH2:35][O:34][C:33]1[CH:47]=[CH:48][C:49]([CH2:51][CH2:2][CH2:1][NH:3][C:4]2[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=2[C@@H:14]2[CH2:23][CH2:22][C:21]3[CH:20]=[C:19]([OH:24])[CH:18]=[CH:17][C:16]=3[CH2:15]2)=[CH:50][C:32]=1[F:31]

Participants

3

Reactant 2

HCID 57934541pivalic acid (R)-6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl esterHCID 57934591Tert-butyl[2-(2-fluoro-4-formylphenoxy)-1,1-dimethylethyl]carbamate

Product 1

HCID 66625859(R)-6-{2-{[4-(2-Amino-2-methylpropoxy)-3-fluorobenzyl]ethylamino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 51.2%

Procedure

Synthesized from pivalic acid (R)-6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (20 mg) and tert-butyl [2-(2-fluoro-4-formylphenoxy)-1,1-dimethylethyl]carbamate (72 mg) according to an analogous synthetic method to Example 238 and purified by LC-MS, the title compound (13 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-eff590e3fa924cf8be4b18002d211a1e
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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