Pivalic acid 6-(6-ethylaminobenzo[1,3]dioxol-5-yl)-5,6,7,8-tetrahydronaphthalen-2-yl ester → 6-{6-{[4-(3-Azepan-1-ylpropyl)benzyl]ethylamino}benzo[1,3]dioxol-5-yl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950236Notes

Reaction equation

HRID 1950236 reaction equation
[CH2:1]([NH:3][C:4]1[C:5]([CH:13]2[CH2:22][CH2:21][C:20]3[CH:19]=[C:18]([O:23]C(=O)C(C)(C)C)[CH:17]=[CH:16][C:15]=3[CH2:14]2)=[CH:6][C:7]2[O:11][CH2:10][O:9][C:8]=2[CH:12]=1)[CH3:2].Cl.[N:31]1([CH2:38][CH2:39][CH2:40][C:41]2[CH:49]=[CH:48][C:44]([C:45](O)=O)=[CH:43][CH:42]=2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1>>[N:31]1([CH2:38][CH2:39][CH2:40][C:41]2[CH:49]=[CH:48][C:44]([CH2:45][CH2:2][CH2:1][NH:3][C:4]3[C:5]([CH:13]4[CH2:22][CH2:21][C:20]5[CH:19]=[C:18]([OH:23])[CH:17]=[CH:16][C:15]=5[CH2:14]4)=[CH:6][C:7]4[O:11][CH2:10][O:9][C:8]=4[CH:12]=3)=[CH:43][CH:42]=2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

3

Reactant 2

HCID 57934012Pivalic acid 6-(6-ethylaminobenzo[1,3]dioxol-5-yl)-5,6,7,8-tetrahydronaphthalen-2-yl esterHCID 666269404-(3-Azepan-1-ylpropyl)benzoic acid hydrochloride

Product 1

HCID 666279356-{6-{[4-(3-Azepan-1-ylpropyl)benzyl]ethylamino}benzo[1,3]dioxol-5-yl}-5,6,7,8-tetrahydronaphthalen-2-olYield 58.5%

Procedure

Synthesized from pivalic acid 6-(6-ethylaminobenzo[1,3]dioxol-5-yl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (40 mg) and 4-(3-azepan-1-ylpropyl)benzoic acid hydrochloride (80 mg) according to an analogous synthetic method to Example 337 described below, the title compound (32 mg) was obtained.

Sources & evidence

ORD record
ord-bd9a6540751a43f19dd7b1913549bc9d
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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