2-chloro-N-methyl-N-[(R)-tetrahydrofuran-2-ylmethyl]acetamide → (R)-6-{2-{Ethyl{3-fluoro-4-{2-{methyl[(R)-tetrahydrofuran-2-ylmethyl]amino}ethoxy}benzyl}amino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950558Notes

Reaction equation

HRID 1950558 reaction equation
[CH2:1]([N:3]([C:31](=O)[C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([F:39])[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[CH2:42][C:43]([N:45]([CH3:52])[CH2:46][C@H:47]1[CH2:51][CH2:50][CH2:49][O:48]1)=O>>[CH2:1]([N:3]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:42][CH2:43][N:45]([CH3:52])[CH2:46][C@H:47]2[CH2:51][CH2:50][CH2:49][O:48]2)=[C:34]([F:39])[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 579341112-chloro-N-methyl-N-[(R)-tetrahydrofuran-2-ylmethyl]acetamideHCID 57934194Pivalic acid (R)-6-{2-[ethyl(3-fluoro-4-hydroxybenzoyl)amino]-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 57933774(R)-6-{2-{Ethyl{3-fluoro-4-{2-{methyl[(R)-tetrahydrofuran-2-ylmethyl]amino}ethoxy}benzyl}amino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 40.2%

Procedure

Synthesized from pivalic acid (R)-6-{2-[ethyl(3-fluoro-4-hydroxybenzoyl)amino]-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (15 mg) and 2-chloro-N-methyl-N—[(R)-tetrahydrofuran-2-ylmethyl]acetamide (10 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (6.5 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-712ee26b80374bcb970c89d4b9764147
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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