Formic Acid → HCID 86651029, compound

HRID 508576Notes

Reaction equation

HRID 508576 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:22](OC)=[O:23])[CH:18]=3)[CH2:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1.Cl.[NH2:29][OH:30].[OH-].[K+].C(O)=O>CO.CS(C)=O>[OH:30][NH:29][C:22]([C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[CH2:13][N:12]([C:10]([NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:27])[F:26])[CH:4]=1)=[O:11])[CH2:21][CH2:20]2)=[O:23]

Participants

7

Reactant 4

HCID 284Formic AcidHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 66970334HCID 66970334, compound

Product 1

HCID 86651029HCID 86651029, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 2-(3-(trifluoromethyl)phenylcarbamoyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (obtained in step 1) in methanol (1 mL) was added hydroxylamine hydrochloride (40 mg, 0.5 mmol) and potassium hydroxide (100 mg, 2 mmol). The reactions were left to stir for 2 hours at 80° C. Upon cooling to room temperature, the reaction was quenched with the addition of formic acid (75 μL, 2 mmol) and the solvents were evaporated to dryness. The residue obtained was dissolved in DMSO (1 mL), the residual solids removed by filtration and the solution purified via Gilson prep-HPLC to afford a white solid (4.2 mg, 11% over 2 steps). LCMS (FA) ES+ 380.

Workup

  1. waitThe reactions were left
  2. temperatureUpon cooling to room temperature
  3. customthe solvents were evaporated to dryness
  4. customThe residue obtained
  5. customthe residual solids removed by filtration
  6. customthe solution purified via Gilson
  7. customto afford a white solid (4.2 mg, 11% over 2 steps)

Sources & evidence

ORD record
ord-ea12845fa9a744b8ba6e5faa523ce514
Source dataset
uspto-grants-2015_08
Patent number
US09096518B2

Reaction notes

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