4,4-Dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydronaphthalen-1(2H)-one → 7-{2-[4-(2-hydroxyethylamino)piperidin-1-yl]thiazol-4-yl}-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one

HRID 1401775Notes

Reaction equation

HRID 1401775 reaction equation
Br[C:2]1[N:3]=[C:4]([N:7]2[CH2:12][CH2:11][CH:10]([NH:13][CH2:14][CH2:15][OH:16])[CH2:9][CH2:8]2)[S:5][CH:6]=1.[CH3:17][C:18]1([CH3:38])[C:27]2[C:22](=[CH:23][C:24](B3OC(C)(C)C(C)(C)O3)=[CH:25][CH:26]=2)[C:21](=[O:37])[CH2:20][CH2:19]1>>[OH:16][CH2:15][CH2:14][NH:13][CH:10]1[CH2:11][CH2:12][N:7]([C:4]2[S:5][CH:6]=[C:2]([C:24]3[CH:23]=[C:22]4[C:27]([C:18]([CH3:38])([CH3:17])[CH2:19][CH2:20][C:21]4=[O:37])=[CH:26][CH:25]=3)[N:3]=2)[CH2:8][CH2:9]1

Participants

3

Reactant 2

HCID 673232734,4-Dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydronaphthalen-1(2H)-oneHCID 673233402-(1-(4-Bromothiazol-2-yl)piperidin-4-ylamino)ethanol

Product 1

HCID 673769197-{2-[4-(2-hydroxyethylamino)piperidin-1-yl]thiazol-4-yl}-4,4-dimethyl-3,4-dihydro-2H-naphthalen-1-one

Procedure

The preparation is carried out as already described above starting from 100 mg (0.27 mmol) of 2-[1-(4-bromothiazol-2-yl)piperidin-4-ylamino]ethanol (preparation already described above) and 88 mg (0.29 mmol) of 4,4-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-naphthalen-1-one. The product was purified by means of flash chromatography on silica gel.

Workup

  1. custompreparation
  2. customThe product was purified by means of flash chromatography on silica gel

Sources & evidence

ORD record
ord-22ed3085e3eb4814aa37e581afddd375
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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