1-(Chloroacetyl)pyrrolidine → 6-{2-{Isopropyl[4-(2-pyrrolidin-1-ylethoxy)benzyl]amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1434188Notes

Reaction equation

HRID 1434188 reaction equation
[OH:1][C:2]1[CH:38]=[CH:37][C:5]([C:6]([N:8]([CH:34]([CH3:36])[CH3:35])[C:9]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=2[CH:17]2[CH2:26][CH2:25][C:24]3[CH:23]=[C:22]([O:27]C(=O)C(C)(C)C)[CH:21]=[CH:20][C:19]=3[CH2:18]2)=O)=[CH:4][CH:3]=1.Cl[CH2:40][C:41]([N:43]1[CH2:47][CH2:46][CH2:45][CH2:44]1)=O>>[CH:34]([N:8]([CH2:6][C:5]1[CH:37]=[CH:38][C:2]([O:1][CH2:40][CH2:41][N:43]2[CH2:47][CH2:46][CH2:45][CH2:44]2)=[CH:3][CH:4]=1)[C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[CH:17]1[CH2:18][CH2:19][C:24]2[CH:23]=[C:22]([OH:27])[CH:21]=[CH:20][C:25]=2[CH2:26]1)([CH3:36])[CH3:35]

Participants

3

Reactant 2

HCID 884401-(Chloroacetyl)pyrrolidineHCID 57933955Pivalic acid 6-{2-[(4-hydroxybenzoyl)isopropylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 579338156-{2-{Isopropyl[4-(2-pyrrolidin-1-ylethoxy)benzyl]amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 80.1%

Procedure

Synthesized from pivalic acid 6-{2-[(4-hydroxybenzoyl)isopropylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (30 mg) and 2-chloro-1-pyrrolidin-1-ylethanone (17 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (24 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-0e44197e3c49474484e95d584f1da7af
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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