2,2,2-Trichloroethyl chloroformate → HCID 67254836, compound

HRID 1711674Notes

Reaction equation

HRID 1711674 reaction equation
C(=O)(O)[O-].[Na+].[NH2:6][C:7]1[N:11]([C:12]2[CH:13]=[C:14]([CH2:22][C:23]([NH2:25])=[O:24])[C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:10]=[C:9]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:8]=1.[C:30](Cl)([O:32][CH2:33][C:34]([Cl:37])([Cl:36])[Cl:35])=[O:31]>C(OCC)(=O)C>[NH2:25][C:23](=[O:24])[CH2:22][C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[C:12]([N:11]2[C:7]([NH:6][C:30](=[O:31])[O:32][CH2:33][C:34]([Cl:37])([Cl:36])[Cl:35])=[CH:8][C:9]([C:26]([CH3:29])([CH3:28])[CH3:27])=[N:10]2)[CH:13]=1

Participants

5

Reactant 3

HCID 870632,2,2-Trichloroethyl chloroformateHCID 516892Sodium BicarbonateHCID 67252319HCID 67252319, compound

Product 1

HCID 67254836HCID 67254836, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of saturated sodium bicarbonate (20 mL), ethyl acetate (20 mL) and 2-(3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)naphthalen-1-yl)acetamide (300 mg, 0.931 mmol) was added Troc-Cl (296 mg, 1.40 mmol). The mixture was stirred vigorously overnight. The mixture was diluted with ethyl acetate (30 mL) and the organic phase was separated, washed with 5% citric acid (30 mL) and brine (30 mL), dried (Na2SO4) and concentrated in vacuo to give a solid which was triturated with ethyl acetate and filtered to provide 2,2,2-trichloroethyl 1-(4-(2-amino-2-oxoethyl)naphthalen-2-yl)-3-tert-butyl-1H-pyrazol-5-ylcarbamate (241 mg, 52% yield). MS (ESI) m/z: 499.0 (M+H+).

Workup

  1. customthe organic phase was separated
  2. washwashed with 5% citric acid (30 mL) and brine (30 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give a solid which
  6. customwas triturated with ethyl acetate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-cf11174becf64af28382f14e07ee1a81
Source dataset
uspto-grants-2010_09
Patent number
US07790756B2

Reaction notes

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