Diisopropylethylamine → HCID 86686691, compound

HRID 75587Notes

Reaction equation

HRID 75587 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3].[C:10]([C:14]1[CH:15]=[C:16]([NH2:34])[N:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][N:26]3[CH2:31][CH2:30][C:29]([F:33])([F:32])[CH2:28][CH2:27]3)[CH:20]=2)[N:18]=1)([CH3:13])([CH3:12])[CH3:11].CCN(C(C)C)C(C)C>C1COCC1>[Cl:7][C:6]([Cl:9])([Cl:8])[CH2:5][O:4][C:2](=[O:3])[NH:34][C:16]1[N:17]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][N:26]3[CH2:31][CH2:30][C:29]([F:33])([F:32])[CH2:28][CH2:27]3)[CH:20]=2)[N:18]=[C:14]([C:10]([CH3:12])([CH3:13])[CH3:11])[CH:15]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 866866905-tert-Butyl-2-[3-(4,4-difluoro-piperidin-1-ylmethyl)-phenyl]-2H-pyrazol-3-ylamine

Product 1

HCID 86686691HCID 86686691, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,2,2-Trichloroethyl chloroformate (0.077 mL, 0.57 mmol) was added to a solution of Intermediate 12c (200 mg, 0.57 mmol) and DIPEA (0.31 mL, 1.81 mmol) in THF (5 mL), and the mixture stirred for 3 h. The mixture was then partitioned between water (10 mL) and EtOAc (3×15 mL), and the combined organic extracts dried (Na2SO4). The solvent was evaporated and the residue triturated under pentane and filtered to give the title compound as a yellow solid (215 mg, 72%). LCMS (Method 1): Rt 2.89 min, m/z 523/525 [MH+]

Workup

  1. customThe mixture was then partitioned between water (10 mL) and EtOAc (3×15 mL)
  2. dry with materialthe combined organic extracts dried (Na2SO4)
  3. customThe solvent was evaporated
  4. customthe residue triturated under pentane
  5. filtrationfiltered

Sources & evidence

ORD record
ord-d96ea78c704f4e75b06ccdf6bd85d60b
Source dataset
uspto-grants-2014_09
Patent number
US08835431B2

Reaction notes

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