Pyrrolidine → HCID 69308874, compound

HRID 860470Notes

Reaction equation

HRID 860470 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[N:11]([C:22]([CH2:25][CH3:26])=[CH:23][CH:24]=3)[N:12]=[C:13]([C:19]([OH:21])=O)[C:14]=2[S:15]([CH3:18])(=[O:17])=[O:16])[CH:6]=[CH:7][CH:8]=1)#[N:2].[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[CH2:25]([C:22]1[N:11]2[N:12]=[C:13]([C:19]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[O:21])[C:14]([S:15]([CH3:18])(=[O:17])=[O:16])=[C:9]([C:5]3[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=3)[C:1]#[N:2])[C:10]2=[CH:24][CH:23]=1)[CH3:26]

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69308744HCID 69308744, compound

Product 1

HCID 69308874HCID 69308874, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(3-cyanophenyl)-7-ethyl-3-(methylsulfonyl)pyrrolo[1,2-b]pyridazine-2-carboxylic acid (40.0 mg), pyrrolidine (10.8 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (31.1 mg), and 1-hydroxybenzotriazole (21.9 mg) in N,N-dimethylformamide (1 mL) was stirred for 6 hour at room temperature. The mixture was partitioned between ethyl acetate (20 mL) and 1N hydrochloric acid (10 mL). The organic layer was washed with water (10 mL) three times, saturated sodium bicarbonate (10 mL), and brine, dried, and evaporated to give 3-[7-ethyl-3-(methylsulfonyl)-2-(1-pyrrolidinylcarbonyl)pyrrolo[1,2-b]pyridazin-4-yl]benzonitrile as an yellow solid (35.6 mg).

Workup

  1. customThe mixture was partitioned between ethyl acetate (20 mL) and 1N hydrochloric acid (10 mL)
  2. washThe organic layer was washed with water (10 mL) three times, saturated sodium bicarbonate (10 mL), and brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-bb3ee9d9c4fc4dc1a90128fc6fe21977
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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