Acetyl chloride → HCID 18545791, compound

HRID 275724Notes

Reaction equation

HRID 275724 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[NH:23][CH2:22]4)[CH2:15][CH:16]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38]>C1COCC1>[C:37]([N:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]([CH2:20][CH2:19][CH2:18][CH2:17][N:14]2[CH2:13][CH:12]=[C:11]([C:6]3[C:5]4[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=4)[NH:8][CH:7]=3)[CH2:16][CH2:15]2)[CH2:22]1)(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 18545800HCID 18545800, compound

Product 1

HCID 18545791HCID 18545791, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

A mixture of 6-chloro-3-[1-[4-(2,3-dihydro-1H-indol-3-yl)butan-1-yl]-1,2,3,6-tetrahydropyridin-4-yl]-1H-indole 30b (4.9 g), triethylamine (3.7 g), and THF (200 ml) was cooled (5° C.), and the mixture was added a solution of acetyl chloride (1.0 g) in THF (50 ml). The reaction mixture was allowed to warm to room temperature, filtered and concentrated in vacuo. The residue was purified on silica gel eluted with ethyl acetate-ethanol-triethylamine (90:10:5) to give the crude product, which was recrystallized (methanol-ethyl acetate) to give the title compound (2.7 g).

Workup

  1. temperatureto warm to room temperature
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified on silica gel
  5. washeluted with ethyl acetate-ethanol-triethylamine (90:10:5)
  6. customto give the crude product, which
  7. customwas recrystallized (methanol-ethyl acetate)

Sources & evidence

ORD record
ord-e0371b5287d74719b9a21fb0806dd8cf
Source dataset
uspto-grants-2002_03
Patent number
US06352988B2

Reaction notes

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