Ammonia → HCID 66633948, compound

HRID 403528Notes

Reaction equation

HRID 403528 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]([C:10](O)=[O:11])=[CH:8][C:7]([C:13]2[N:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:6]1.C(Cl)(=O)C(Cl)=O.C[N:30](C=O)C.N.O1CCOCC1>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:9]([C:10]([NH2:30])=[O:11])=[CH:8][C:7]([C:13]2[N:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[N:6]1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 6228DimethylformamideHCID 312751,4-DioxaneHCID 65578Oxalyl chlorideHCID 66633767HCID 66633767, compound

Product 1

HCID 66633948HCID 66633948, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 1-(2-fluorobenzyl)-3-(pyrimidin-2-yl)-1H-pyrazole-5-carboxylic acid, intermediate 9 (133 mg, 1 equiv) and oxalyl chloride (60 μL, 1.5 equiv) in chloroform (2.2 ml), was added DMF (3 μL, 0.1 equiv). The mixture was allowed to stir at room temperature and until the bubbling ceased. Then, to this mixture, was added a solution of 0.5 M ammonia in dioxane (2.7 ml, 3.0 equiv). The mixture was stirred at room temperature for 1 h. It was concentrated under vacuum. The resulting residue was suspended in ethyl acetate (200 ml) and washed with saturated solution of sodium bicarbonate (50 ml×2). The organic layer was washed with brine (10 ml), dried, filtered and evaporated to give 120 mg of 1-(2-fluorobenzyl)-3-(pyrimidin-2-yl)-1H-pyrazole-5-carboxamide (91%) as an orange solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 h
  2. concentrationIt was concentrated under vacuum
  3. washwashed with saturated solution of sodium bicarbonate (50 ml×2)
  4. washThe organic layer was washed with brine (10 ml)
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-cb37a547ff6f4e4d85a45c35386500e2
Source dataset
uspto-grants-2014_06
Patent number
US08748442B2

Reaction notes

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