Methyl chloroformate → HCID 86729404, compound

HRID 521233Notes

Reaction equation

HRID 521233 reaction equation
FC(F)(F)C([O-])=O.[C:8]([C:11]1[C:12]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([C:35]([F:38])([F:37])[F:36])(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[N:13][N:14]([C:16]2([CH2:22][C:23]#[N:24])[CH2:21][CH2:20][NH2+:19][CH2:18][CH2:17]2)[CH:15]=1)(=[O:10])[NH2:9].CCN(C(C)C)C(C)C.Cl[C:49]([O:51][CH3:52])=[O:50]>C(Cl)Cl>[C:8]([C:11]1[C:12]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([C:35]([F:38])([F:36])[F:37])(=[O:33])=[O:34])=[CH:28][CH:27]=2)=[N:13][N:14]([C:16]2([CH2:22][C:23]#[N:24])[CH2:21][CH2:20][N:19]([C:49]([O:51][CH3:52])=[O:50])[CH2:18][CH2:17]2)[CH:15]=1)(=[O:10])[NH2:9]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 86729405HCID 86729405, compound

Product 1

HCID 86729404HCID 86729404, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[4-Carbamoyl-3-({4-[(trifluoromethyl)sulfonyl]phenyl}amino)-1H-pyrazol-1-yl]-4-(cyanomethyl)piperidinium trifluoroacetate (Intermediate #38-7) (30 mg, 0.053 mmol) was dissolved in DCM (1.0 mL). DIPEA (0.055 mL, 0.32 mmol) was added, followed by methyl chloroformate (0.024 mL, 0.32 mmol). The resulting mixture was allowed to stir at ambient temperature for 30 minutes. The solvent was removed in vacuo and the crude residue was purified by reverse-phase preparative HPLC (MeCN/water, with 0.1% v/v TFA modifier). Desired fractions were identified, combined, and concentrated in vacuo to afford the title compound, Example #27-1, as a solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude residue was purified by reverse-phase preparative HPLC (MeCN/water
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1dc7e32be7f24a6e9dd5128abc7acdee
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

Loading…