Chloroacetyl chloride → HCID 66588025, compound

HRID 530923Notes

Reaction equation

HRID 530923 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8]2[CH2:15][CH2:16][NH:17][CH2:18][C:7]1=2.C(N(CC)CC)C.[Cl:29][CH2:30][C:31](Cl)=[O:32].C(=O)(O)[O-].[Na+]>C1COCC1>[Cl:29][CH2:30][C:31]([N:17]1[CH2:16][CH2:15][C:8]2[C:9]3[C:10]([N:6]([CH2:5][C:4]4[CH:19]=[CH:20][CH:21]=[C:2]([F:1])[CH:3]=4)[C:7]=2[CH2:18]1)=[N:11][CH:12]=[CH:13][CH:14]=3)=[O:32]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 86682560HCID 86682560, compound

Product 1

HCID 66588025HCID 66588025, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 9-(3-fluorobenzyl)-6,7,8,9-tetrahydro-5H-pyrido[4′,3′:4,5]pyrrolo[2,3-b]pyridine (500 mg) produced by operation in accordance with Reference manufacturing example 1 in THF (10 mL) were sequentially added triethylamine (0.59 mL) and chloroacetyl chloride (0.135 mL), and the mixture was stirred for 30 minutes. The reaction mixture was poured into an aqueous saturated sodium bicarbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain the title compound (459 mg) having the following physical property values.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-653b565891f6482a8c33177073dcf31c
Source dataset
uspto-grants-2016_05
Patent number
US09353113B2

Reaction notes

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