Diisopropylethylamine → HCID 86657488, compound

HRID 241571Notes

Reaction equation

HRID 241571 reaction equation
I[CH:2]1[C:7](=[O:8])[N:6]([CH3:9])[C@H:5]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[F:17])[C@@H:4]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:3]1.[F:26][C:27]([F:38])([F:37])[C:28]([NH:30][C:31]1[CH:36]=[N:35][CH:34]=[CH:33][N:32]=1)=O.C([N:42](CC)C(C)C)(C)C>CN(C=O)C>[F:17][C:11]1[CH:12]=[CH:13][C:14]([F:16])=[CH:15][C:10]=1[C@@H:5]1[C@@H:4]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:3][C@@H:2]([N:35]2[CH2:34][CH2:33][N:32]3[N:42]=[C:28]([C:27]([F:38])([F:37])[F:26])[N:30]=[C:31]3[CH2:36]2)[C:7](=[O:8])[N:6]1[CH3:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 198729Acetamide, 2,2,2-trifluoro-N-pyrazinyl-HCID 86657489HCID 86657489, compound

Product 1

HCID 86657488HCID 86657488, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
47 °C

Procedure

tert-Butyl [(2R,3S)-5-iodo-2-(2,5-difluorophenyl)-1-methyl-6-oxopiperidin-3-yl]carbamate (560 mg, 1.201 mmol) was dissolved in DMF (5 mL) at room temperature. 2,2,2-Trifluoro-N-pyrazin-2-ylacetamide (300 mg, 1.561 mmol) was added, followed by N,N-diisopropylethylamine (0.420 mL, 2.402 mmol). The reaction was heated at 47° C. for 4.5 h. The DMF was removed by evaporation under reduced pressure, the residue was purified by column chromatography on silica gel Biotage 25M™, eluting with CH2Cl2/MeOH/aqueous NH3 (gradient from 4% to 8%) to give the title compound. LC-MS: 474.83 (M+1).

Workup

  1. customThe DMF was removed by evaporation under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel Biotage 25M™
  3. washeluting with CH2Cl2/MeOH/aqueous NH3 (gradient from 4% to 8%)

Sources & evidence

ORD record
ord-c793c5187df346418e10d4e9d776c8df
Source dataset
uspto-grants-2014_02
Patent number
US08653059B2

Reaction notes

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