Acetyl chloride → HCID 59457798, compound

HRID 1711782Notes

Reaction equation

HRID 1711782 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:17]=[CH:18][C:19]4[N:20]([C:22]([CH:25]5[CH2:29][CH2:28][NH:27][CH2:26]5)=[N:23][N:24]=4)[CH:21]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1.[C:30](Cl)(=[O:32])[CH3:31]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:17]=[CH:18][C:19]4[N:20]([C:22]([CH:25]5[CH2:29][CH2:28][N:27]([C:30](=[O:32])[CH3:31])[CH2:26]5)=[N:23][N:24]=4)[CH:21]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 59457794HCID 59457794, compound

Product 1

HCID 59457798HCID 59457798, compoundYield 17.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 6-(4-fluorophenyl)-5-(3-(pyrrolidin-3-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)imidazo[2,1-b]oxazole (0.100 g, 0.26 mmol; Example #M.1.1.3) in DCM (5 mL) was added TEA (0.04 mL, 0.26 mmol) and acetyl chloride (0.02 mL, 0.26 mmol). The reaction mixture was stirred at ambient temperature for about 16 h. The crude reaction mixture was purified by flash chromatography (silica gel; DCM/MeOH gradient from 99:1 to 90:10) to afford the title compound (0.02 g, 17%). LC/MS (Table 1, Method a) Rt=1.79 min; MS m/z: 431.1 (M+H)+.

Workup

  1. customThe crude reaction mixture
  2. customwas purified by flash chromatography (silica gel; DCM/MeOH gradient from 99:1 to 90:10)

Sources & evidence

ORD record
ord-a9e1cef762264472a0e2683de4cb96a2
Source dataset
uspto-grants-2010_09
Patent number
US07790741B2

Reaction notes

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