2,4,6-Trimethylpyridine → N-(4-(((2-cyanobenzo[d]thiazol-6-yl)oxy)methyl)phenyl)-3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide

HRID 921509Notes

Reaction equation

HRID 921509 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])[CH2:11][C:12]([CH3:25])([C:14]2[C:19](=[O:20])[C:18]([CH3:21])=[C:17]([CH3:22])[C:16](=[O:23])[C:15]=2[CH3:24])[CH3:13])=[CH:5][CH:4]=1.[OH:27][C:28]1[CH:38]=[CH:37][C:31]2[N:32]=[C:33]([C:35]#[N:36])[S:34][C:30]=2[CH:29]=1.N1C(C)=CC(C)=CC=1C>C1COCC1>[C:35]([C:33]1[S:34][C:30]2[CH:29]=[C:28]([O:27][CH2:2][C:3]3[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])[CH2:11][C:12]([CH3:25])([C:14]4[C:19](=[O:20])[C:18]([CH3:21])=[C:17]([CH3:22])[C:16](=[O:23])[C:15]=4[CH3:24])[CH3:13])=[CH:5][CH:4]=3)[CH:38]=[CH:37][C:31]=2[N:32]=1)#[N:36]

Participants

5

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 98819122-Cyano-6-hydroxybenzothiazoleHCID 86685024N-(4-(Bromomethyl)phenyl)-3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide

Product 1

HCID 71285603N-(4-(((2-cyanobenzo[d]thiazol-6-yl)oxy)methyl)phenyl)-3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamideYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(4-(bromomethyl)phenyl)-3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide (0.23 g, 0.57 mmol), 6-hydroxy-2-cyanobenzothiazole (0.15 g, 0.86 mmol), 2,4,6-collidine (0.125 ml) and Ag2CO3 (0.24 g, 0.86 mmol) in 15 ml of dry THF was stirred at room temperature over night. After removal of solid by filtration, the compound was purified by silica chromatography using heptane and ethyl acetate as eluent to give a yield of 40%. The product was further purified by HPLC to remove small contamination of 2-cyano-6-hydroxybenzothiazole. 1H NMR (300 MHz, CD2Cl2) δ 7.4-7.5 (m, 3H), 7.35-7.42 (m, 2H), 7.32 (dd, 1H), 7.25 (s, br, 1H, NH), 7.18 (dd, 1H), 5.15 (s, 2H, CH2O), 2.99 (s, 2H, CH2), 2.14 (s, 3H, CH3), 1.92 (s, 6H, CH3), 1.47 (s, 6H, CH3). MS (m/e): 514.2 (M+).

Workup

  1. customAfter removal of solid
  2. filtrationby filtration
  3. customthe compound was purified by silica chromatography
  4. customto give a yield of 40%
  5. customThe product was further purified by HPLC
  6. customto remove small contamination of 2-cyano-6-hydroxybenzothiazole

Sources & evidence

ORD record
ord-0f495beec1d0428fb1e347dba9f0e192
Source dataset
uspto-grants-2016_03
Patent number
US09273343B2

Reaction notes

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