Dichloromethane → HCID 68803978, compound

HRID 860467Notes

Reaction equation

HRID 860467 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[N:11]([C:28]([CH2:31][CH3:32])=[CH:29][CH:30]=3)[N:12]=[C:13]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:14]=2[CH2:15][CH2:16][CH2:17][CH2:18][C:19](O)=[O:20])[CH:6]=[CH:7][CH:8]=1)#[N:2].Cl.CN(C)[CH2:36][CH2:37][CH2:38][N:39]=[C:40]=[N:41]CC.Cl[CH2:46]Cl>CN(C)C1C=CN=CC=1.O>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[N:11]([C:28]([CH2:31][CH3:32])=[CH:29][CH:30]=3)[N:12]=[C:13]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:14]=2[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([NH:41][C:40]2[CH:46]=[CH:36][CH:37]=[CH:38][N:39]=2)=[O:20])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68802645HCID 68802645, compound

Product 1

HCID 68803978HCID 68803978, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

To a stirred solution of 5-[4-(3-cyanophenyl)-7-ethyl-2-phenylpyrrolo[1,2-b]pyridazin-3-yl]pentanoic acid (60 mg) in dichloromethane (2 ml) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (35.3 mg) and 2-animopyridine (20 mg) and the reaction mixture was stirred for 10 minutes. 4-Dimethylaminopyridine (2 mg) was added and the reaction mixture was stirred at room temperature for 15 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a mixture of ethyl acetate and n-hexane (1:2) to give 5-[4-(3-cyanophenyl)-7-ethyl-2-phenylpyrrolo[1,2-b]pyridazin-3-yl]-N-(2-pyridinyl)pentanamide (55.7 mg) as an yellow amorphous.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 15 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a mixture of ethyl acetate and n-hexane (1:2)

Sources & evidence

ORD record
ord-9153ca51acd34770a066333647452fd3
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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