Pivalic acid 6-{2-[(3-fluoro-4-hydroxybenzoyl)isopropylamino]-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester → 6-{2-{{3-Fluoro-4-[2-(4-methyl-[1,4]diazepan-1-yl)ethoxy]benzyl}isopropylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950371Notes

Reaction equation

HRID 1950371 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][C:38]=1[OH:39])[C:5]([N:7]([CH:33]([CH3:35])[CH3:34])[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH:16]1[CH2:25][CH2:24][C:23]2[CH:22]=[C:21]([O:26]C(=O)C(C)(C)C)[CH:20]=[CH:19][C:18]=2[CH2:17]1)=O.C(O[C:45]([N:47]1[CH2:53][CH2:52][CH2:51][N:50]([C:54](=O)[CH2:55]Cl)[CH2:49][CH2:48]1)=O)(C)(C)C>>[F:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][C:38]=1[O:39][CH2:55][CH2:54][N:50]1[CH2:51][CH2:52][CH2:53][N:47]([CH3:45])[CH2:48][CH2:49]1)[CH2:5][N:7]([CH:33]([CH3:34])[CH3:35])[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH:16]1[CH2:17][CH2:18][C:23]2[CH:22]=[C:21]([OH:26])[CH:20]=[CH:19][C:24]=2[CH2:25]1

Participants

3

Reactant 2

HCID 57934527Pivalic acid 6-{2-[(3-fluoro-4-hydroxybenzoyl)isopropylamino]-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl esterHCID 57934585Tert-butyl 4-(2-chloroacetyl)-1,4-diazepane-1-carboxylate

Product 1

HCID 579339406-{2-{{3-Fluoro-4-[2-(4-methyl-[1,4]diazepan-1-yl)ethoxy]benzyl}isopropylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 59.3%

Procedure

Synthesized from pivalic acid 6-{2-[(3-fluoro-4-hydroxybenzoyl)isopropylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (25 mg) and 4-(2-chloroacetyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (26 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (16 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-45e1bbf3df0a4fbe86f12e82482450e9
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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