Pivalic acid 6-{2-[ethyl(4-hydroxybenzoyl)amino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester → 6-{2-{Ethyl {4-[2-(4-methyl-[1,4]diazepan-1-yl)ethoxy]benzyl}amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950405Notes

Reaction equation

HRID 1950405 reaction equation
[CH2:1]([N:3]([C:29](=O)[C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[CH: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].C(O[C:43]([N:45]1[CH2:51][CH2:50][CH2:49][N:48]([C:52](=O)[CH2:53]Cl)[CH2:47][CH2:46]1)=O)(C)(C)C>>[CH2:1]([N:3]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:53][CH2:52][N:48]2[CH2:49][CH2:50][CH2:51][N:45]([CH3:43])[CH2:46][CH2:47]2)=[CH:32][CH:31]=1)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[CH: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 57934562Pivalic acid 6-{2-[ethyl(4-hydroxybenzoyl)amino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl esterHCID 57934585Tert-butyl 4-(2-chloroacetyl)-1,4-diazepane-1-carboxylate

Product 1

HCID 579338106-{2-{Ethyl {4-[2-(4-methyl-[1,4]diazepan-1-yl)ethoxy]benzyl}amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 44.3%

Procedure

Synthesized from pivalic acid 6-{2-[ethyl(4-hydroxybenzoyl)amino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (20 mg) and 4-(2-chloroacetyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (22 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (9.6 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-258953f1856a45e1b8c1a8ccbe73dfa6
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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