Acetyl chloride → HCID 10096420, compound

HRID 1991079Notes

Reaction equation

HRID 1991079 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][N:10]([C:13](=[O:30])/[CH:14]=[CH:15]/[C:16]3[C:17]([NH:26][C:27](=[O:29])[CH3:28])=[CH:18][C:19]4[C:24]([CH:25]=3)=CC=CC=4)[C@H:9]([CH3:31])[CH2:8]2)=[CH:4][CH:3]=1.CCN(CC)CC.C([Cl:44])(=O)C.C1C[O:48][CH2:47][CH2:46]1>C(=O)([O-])[O-].[Na+].[Na+]>[Cl:44][C:19]1[C:24]([O:48][CH2:47][CH3:46])=[CH:25][C:16](/[CH:15]=[CH:14]/[C:13]([N:10]2[CH2:11][CH2:12][N:7]([CH2:6][C:5]3[CH:32]=[CH:33][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:8][C@H:9]2[CH3:31])=[O:30])=[C:17]([NH:26][C:27](=[O:29])[CH3:28])[CH:18]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10388824HCID 10388824, compound

Product 1

HCID 10096420HCID 10096420, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Procedure

(E)-3-(2-Amino-4-chloro-5-ethoxyphenyl)-1-[(R)-4-(4-fluorobenzyl)-2-meyhyl-piperazin-1-yl]-propenone (prepared by amide coupling and SnCl2 reduction as described in example 30) (0.1 g, 0.23 mmol) was dissolved in 10 ml THF and 38.7 μl (0.28 mmol) NEt3 and 16.5 μl (0.23 mmol) acetyl chloride were added. This mixture was stirred for 20 min. at room temperature. Then the mixture was diluted with 10 ml saturated sodium carbonate solution and extracted with ethyl acetate. The title compound was purified by chromatography (SiO2, ethyl acetate/MeOH/NH3conc. 95/5/0.5) and was isolated as a pale solid (89 mg, 81%)

Workup

  1. extractionextracted with ethyl acetate
  2. customThe title compound was purified by chromatography (SiO2, ethyl acetate/MeOH/NH3conc. 95/5/0.5)

Sources & evidence

ORD record
ord-7bb89f26afd74a7c86ab73e5028dd472
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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