Hydrochloric Acid → methyl N-[[2-chloro-5-[1-(3,4-dihydro-3-oxo-2H-1-benzopyran-6-yl)-1H-pyrazol-3-yl]phenyl]methyl]carbamate

HRID 1408434Notes

Reaction equation

HRID 1408434 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][N:10]([C:13]3[CH:14]=[CH:15][C:16]4[O:25][CH2:24][C:19]5(OCC[O:20]5)[CH2:18][C:17]=4[CH:26]=3)[N:9]=2)=[CH:4][C:3]=1[CH2:27][NH:28][C:29](=[O:32])[O:30][CH3:31].Cl>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][N:10]([C:13]3[CH:14]=[CH:15][C:16]4[O:25][CH2:24][C:19](=[O:20])[CH2:18][C:17]=4[CH:26]=3)[N:9]=2)=[CH:4][C:3]=1[CH2:27][NH:28][C:29](=[O:32])[O:30][CH3:31]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67151202methyl N-[[2-chloro-5-(1-spiro[2H-1-benzopyran-3(4H), 2'-[1,3]dioxolan]-6-yl-1H-pyrazol-3-yl)phenyl]methyl]carbamate2×

Product 1

HCID 67151129methyl N-[[2-chloro-5-[1-(3,4-dihydro-3-oxo-2H-1-benzopyran-6-yl)-1H-pyrazol-3-yl]phenyl]methyl]carbamateYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl N-[[2-chloro-5-(1-spiro[2H-1-benzopyran-3(4H), 2′-[1,3]dioxolan]-6-yl-1H-pyrazol-3-yl)phenyl]methyl]carbamate (i.e. the product of Example 9, Step B) (150 mg, 0.32 mmol) in acetone (15 mL) was added 3N HCl (4.5 mL). The reaction mixture was heated at 85° C. for 16 hrs when TLC analysis (50% ethyl acetate/pet ether) showed completion of reaction. The reaction mixture was cooled and the solvent was concentrated under vacuum. The resultant residue was partitioned between water and ethyl acetate. The organic phase was washed with water, brine, dried over Na2SO4 and concentrated under vacuum to give the title compound, a compound of the present invention, (90 mg, 68% yield) as a solid.

Workup

  1. customcompletion of reaction
  2. temperatureThe reaction mixture was cooled
  3. concentrationthe solvent was concentrated under vacuum
  4. customThe resultant residue was partitioned between water and ethyl acetate
  5. washThe organic phase was washed with water, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-52ac1ee65a0840afae2eca54cb4fe130
Source dataset
uspto-grants-2014_12
Patent number
US08921360B2

Reaction notes

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