2-chloro-N-ethyl-N-methylacetamide → (R)-6-{2-{Ethyl {4-[2-(ethylmethylamino)ethoxy]-3-fluorobenzyl}amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1434337Notes

Reaction equation

HRID 1434337 reaction equation
[CH2:1]([N:3]([C:29](=O)[C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([F:37])[CH:31]=1)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[C@@H:12]1[CH2:21][CH2:20][C:19]2[CH:18]=[C:17]([O:22]C(=O)C(C)(C)C)[CH:16]=[CH:15][C:14]=2[CH2:13]1)[CH3:2].Cl[CH2:40][C:41]([N:43]([CH2:45][CH3:46])[CH3:44])=O>>[CH2:1]([N:3]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:40][CH2:41][N:43]([CH2:45][CH3:46])[CH3:44])=[C:32]([F:37])[CH:31]=1)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[C@@H:12]1[CH2:21][CH2:20][C:19]2[CH:18]=[C:17]([OH:22])[CH:16]=[CH:15][C:14]=2[CH2:13]1)[CH3:2]

Participants

3

Reactant 2

HCID 222346982-chloro-N-ethyl-N-methylacetamideHCID 57933882pivalic acid (R)-6-{2-[ethyl(3-fluoro-4-hydroxybenzoyl)amino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 58023073(R)-6-{2-{Ethyl {4-[2-(ethylmethylamino)ethoxy]-3-fluorobenzyl}amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 68.4%

Procedure

Synthesized from pivalic acid (R)-6-{2-[ethyl(3-fluoro-4-hydroxybenzoyl)amino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (15 mg) and 2-chloro-N-ethyl-N-methylacetamide (7.9 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (10 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-a2cbe45fd71d40d8a12c0c1d53edceb4
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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