Dimethylformamide dimethyl acetal → HCID 66749245, compound

HRID 2401822Notes

Reaction equation

HRID 2401822 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[S:10][C:11]=2[C:12](=[O:14])[CH3:13])=[CH:4][CH:3]=1.CO[CH:25](OC)[N:26]([CH3:28])[CH3:27]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)[S:10][C:11]=2[C:12](=[O:14])/[CH:13]=[CH:25]/[N:26]([CH3:28])[CH3:27])=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 66747676HCID 66747676, compound

Product 1

HCID 66749245HCID 66749245, compoundYield 90.5%

Procedure

A solution of 1-(4-(4-chlorobenzyl)-2-(pyridin-4-yl)thiazol-5-yl)ethanone (370 mg, 1.12 mmol) in 1,1-dimethoxy-N,N-dimethylmethanamine (10.0 mL, 75.3 mmol) was heated to 80 degrees for 6 hours. The reaction was cooled and concentrated in vacuo. The residue was purified by silica gel chromatography (EA/DCM=0/100→100/0) to give 389 mg (90% yield) of the title compound as a yellow solid. LC/MS (FA) ES+ 384, 386. 1H NMR (300 MHz, CDCl3) δ: 8.70-8.68 (m, 2H), 7.81-7.75 (m, 3H), 7.36-7.33 (m, 2H), 7.26-7.24 (m, 2H), 5.41 (d, 1H, J=12.3 Hz), 4.55 (s, 2H), 3.16 (s, 3H), 2.88 (s, 3H).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel chromatography (EA/DCM=0/100→100/0)

Sources & evidence

ORD record
ord-7cbf7ba2e1e641729a003aa5e529f3e0
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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