1,2-Dichloroethane → HCID 58170049, compound

HRID 57707Notes

Reaction equation

HRID 57707 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:10][C:11](=[O:21])[C:12]2[N:13]([N:15]=[C:16]([C:18](O)=[O:19])[CH:17]=2)[CH:14]=1.C(Cl)CCl.C1C=CC2N(O)N=[N:32]C=2C=1.N.O1CCOCC1>ClCCl.CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:10][C:11](=[O:21])[C:12]2[N:13]([N:15]=[C:16]([C:18]([NH2:32])=[O:19])[CH:17]=2)[CH:14]=1

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 312751,4-DioxaneHCID 757711-HydroxybenzotriazoleHCID 58170051HCID 58170051, compound

Product 1

HCID 58170049HCID 58170049, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

360 mg (1.11 mmol) of 6-(2,4-dichlorophenyl)-4-oxo-4,5-dihydropyrazolo[1,5-a]pyrazine-2-carboxylic acid (Example 55A) were initially charged in dichloromethane (30 ml) and DMF (10 ml), and 320 mg (1.67 mmol) of EDC, 225 mg (1.67 mg) HOBt and 407 mg (3.33 mmol) of DMAP were added, followed by 0.5M ammonia in dioxane (2.44 ml, 1.22 mmol). The reaction mixture was stirred at RT for 20 h, the solvent was concentrated, the residue was poured into water (25 ml) and the precipitate was filtered off and washed with water and acetonitrile and dried. Drying gave 260 mg (72% of theory) of the product as a solid.

Workup

  1. concentrationthe solvent was concentrated
  2. additionthe residue was poured into water (25 ml)
  3. filtrationthe precipitate was filtered off
  4. washwashed with water and acetonitrile
  5. customdried
  6. customDrying

Sources & evidence

ORD record
ord-47be18e18b1942dfa48cfc96dabaa46f
Source dataset
uspto-grants-2016_09
Patent number
US09434731B2

Reaction notes

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