Acetyl chloride → HCID 24865070, compound

HRID 506153Notes

Reaction equation

HRID 506153 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[C:16]([C:17]#[N:18])=[CH:15][N:14]=[CH:13][C:12]=3[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.NN.[C:30](Cl)(=[O:32])[CH3:31]>CO.C(Cl)Cl.N1C=CC=CC=1.[Ni]>[C:17]([C:16]1[C:11]([NH:10][C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][CH:2]=[CH:3]3)=[C:12]([C:19]2[CH:20]=[C:21]([NH:25][C:30](=[O:32])[CH3:31])[CH:22]=[CH:23][CH:24]=2)[CH:13]=[N:14][CH:15]=1)#[N:18]

Participants

8

Reactant 3

HCID 6367Acetyl chlorideHCID 9321HydrazineHCID 24864897HCID 24864897, compound

Product 1

HCID 24865070HCID 24865070, compound

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 887MethanolSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1H-indol-5-ylamino)-5-(3-nitrophenyl)nicotinonitrile 151 (9 mg, 0.025 mmol) in MeOH (1 mL) were added hydrazine (20 uL) and Raney-Nickel (2-5 mg). The mixture was stirred for 2 h then filtered through celite and the filtrate was concentrated to give the crude reduced product which was then dissolved in CH2Cl2 (1 mL) and pyridine (20 uL), and acetyl chloride (20 uL) was added. After stirring for 1 h, the reaction mixture was evaporated and the residue was purified by preparative HPLC to give the title compound (4 mg). MS: 366.0 (M+H), HPLC retention time: 1.61 min.(a).

Workup

  1. filtrationthen filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customto give the crude
  4. stirringAfter stirring for 1 h
  5. customthe reaction mixture was evaporated
  6. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-352c6633480e482da840e7ad578f0f5d
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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