Pivalic acid (R)-6-{2-[ethyl(4-hydroxybenzoyl)amino]-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester → (R)-6-{2-{Ethyl {4-{2-{methyl[(S)-tetrahydrofuran-2-ylmethyl]amino}ethoxy}benzyl}amino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 2424118Notes

Reaction equation

HRID 2424118 reaction equation
[CH2:1]([N:3]([C:31](=O)[C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1)[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].Cl[CH2:41][C:42]([N:44]([CH3:51])[CH2:45][C@@H:46]1[CH2:50][CH2:49][CH2:48][O:47]1)=O>>[CH2:1]([N:3]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:41][CH2:42][N:44]([CH3:51])[CH2:45][C@@H:46]2[CH2:50][CH2:49][CH2:48][O:47]2)=[CH:34][CH:33]=1)[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]([OH:24])[CH:18]=[CH:17][C:16]=2[CH2:15]1)[CH3:2]

Participants

3

Reactant 2

HCID 57934042Pivalic acid (R)-6-{2-[ethyl(4-hydroxybenzoyl)amino]-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl esterHCID 579343042-chloro-N-methyl-N-[(S)-tetrahydrofuran-2-ylmethyl]acetamide

Product 1

HCID 58023097(R)-6-{2-{Ethyl {4-{2-{methyl[(S)-tetrahydrofuran-2-ylmethyl]amino}ethoxy}benzyl}amino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 27.7%

Procedure

Synthesized from pivalic acid (R)-6-{2-[ethyl(4-hydroxybenzoyl)amino]-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (16 mg) and 2-chloro-N-methyl-N—[(S)-tetrahydrofuran-2-ylmethyl]acetamide (10 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (4.8 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-4995694588864e7980d32f6c5ef0b80b
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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