Acetyl chloride → HCID 59457690, compound

HRID 2193745Notes

Reaction equation

HRID 2193745 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH:19]=3)[S:13][C:6]=12.CCN(C(C)C)C(C)C.[C:36](Cl)(=[O:38])[CH3:37]>C(Cl)Cl>[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH2:15][CH2:16][N:17]([C:36](=[O:38])[CH3:37])[CH2:18][CH:19]=3)[S:13][C:6]=12

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 59457731HCID 59457731, compound

Product 1

HCID 59457690HCID 59457690, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-1,2,3,6-tetrahydropyridine 268 (400 mg, 1.08 mmol) and DIPEA (0.207 mL, 1.19 mmol) in DCM was added acetyl chloride (0.15 mL, 2.16 mmol) at room temperature and the mixture (that turned homogeneous soon after) was stirred for 1 h. The crude mixture was concentrated under reduced pressure and the residue purified by flash chromatography (5% MeOH to 10% MeOH in DCM) affording 269 (358.2 mg, 0.87 mmol, 80% yield) as a white solid. MS (m/z): (M+1) 414.4 (100%).

Workup

  1. concentrationThe crude mixture was concentrated under reduced pressure
  2. customthe residue purified by flash chromatography (5% MeOH to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-8f235a102ba74f30a448529502ffd534
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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