Hydrochloric Acid → HCID 69306897, compound

HRID 2250593Notes

Reaction equation

HRID 2250593 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](O)=[O:20])[C:14]=2[S:15]([CH3:18])(=[O:17])=[O:16])[CH:6]=[CH:7][CH:8]=1)#[N:2].Cl.[CH3:28][N:29](C)[CH2:30]CCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[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]([N:29]([CH3:30])[CH3:28])=[O:20])[C:14]=2[S:15]([CH3:18])(=[O:16])=[O:17])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 69308744HCID 69308744, compound

Product 1

HCID 69306897HCID 69306897, compoundYield 101.1%

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), diemthylamine hydrochloride (12.4 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (25.2 mg), and 1-hydroxybenzotriazole (21.9 mg) in N,N-dimethylformamide (1 mL) was stirred for 3 hours 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 (10×3 mL), saturated sodium bicarbonate (10 mL), and brine, dried over magnesium sulfate, and evaporated to give 4-(3-cyanophenyl)-7-ethyl-N,N-dimethyl-3-(methylsulfonyl)pyrrolo[1,2-b]pyridazine-2-carboxamide as an yellow solid (43.4 mg, 101%).

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 (10×3 mL), saturated sodium bicarbonate (10 mL), and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-12d25ed7e9c248229b2f82e1eca04d81
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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