(4-Chloro-pyrimidin-2-yl)(2,2,6,6-tetramethyl-piperidin-4-yl)-amine → HCID 57936343, compound

HRID 1435040Notes

Reaction equation

HRID 1435040 reaction equation
C([Si](C)(C)[N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][CH2:16][C:17]([O:20][Si](C(C)(C)C)(C)C)([CH3:19])[CH3:18])[CH:13]=2)[CH:8]=[CH:7]1)(C)(C)C.Cl[C:31]1[CH:36]=[CH:35][N:34]=[C:33]([NH:37][CH:38]2[CH2:43][C:42]([CH3:45])([CH3:44])[NH:41][C:40]([CH3:47])([CH3:46])[CH2:39]2)[N:32]=1>N1C=CC=CC=1>[CH3:19][C:17]([OH:20])([CH2:16][CH2:15][C:12]1[CH:13]=[C:14]2[C:9]([C:8]([C:35]3[CH:36]=[CH:31][N:32]=[C:33]([NH:37][CH:38]4[CH2:43][C:42]([CH3:45])([CH3:44])[NH:41][C:40]([CH3:47])([CH3:46])[CH2:39]4)[N:34]=3)=[CH:7][NH:6]2)=[CH:10][CH:11]=1)[CH3:18]

Participants

4

Reactant 2

HCID 57936167(4-Chloro-pyrimidin-2-yl)(2,2,6,6-tetramethyl-piperidin-4-yl)-amineHCID 69059753HCID 69059753, compound

Product 1

HCID 57936343HCID 57936343, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The title compound was prepared as described in Example 215, starting from 1-(tert-butyl-dimethyl-silanyl)-6-[3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-1H-indole (prepared by Raney-Nickel hydrogenation of (E)-3-(1H-Indol-6-yl)-acrylic acid methyl ester, followed by reaction with MeMgBr (Step A of Method A) and TBDMS protection according to standard procedures) and (4-chloro-pyrimidin-2-yl)-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine, followed by cleavage of the TBDMS protecting groups with HF in pyridine. Yield: 57 mg (17%).

Sources & evidence

ORD record
ord-6beadd60847c41198064e79c556c606a
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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