Pivaloyl chloride → HCID 67267043, compound

HRID 602104Notes

Reaction equation

HRID 602104 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:22]=[CH:21][C:11]([C:12]([NH:14][C@H:15]3[C@H:19]([OH:20])[CH2:18][NH:17][CH2:16]3)=[O:13])=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.[C:32](Cl)(=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34]>CN(C=O)C>[CH3:34][C:33]([CH3:36])([CH3:35])[C:32]([N:17]1[CH2:18][C@@H:19]([OH:20])[C@H:15]([NH:14][C:12](=[O:13])[C:11]2[CH:21]=[CH:22][C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[N:9][CH:10]=2)[CH2:16]1)=[O:37]

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 67070408HCID 67070408, compound

Product 1

HCID 67267043HCID 67267043, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of trans-6-(3-fluorophenyl)-N-[4-hydroxypyrrolidin-3-yl]nicotinamide (50 mg, 0.15 mmol) in DMF (1.0 mL) was added DIPEA (95 mg, 0.32 mmol) and pivaloyl chloride (66 mg, 0.24 mmol). After stirring at rt overnight the mixture was partitioned between ethyl acetate and brine. The organic layer was dried (MgSO4), filtered and the solvent removed to give an oil, which after chromatography (silica, 1% MeOH/EtOAc) gave the product (36 mg, 63%). HRMS (M+H)=386.1880 expected, 386.1914 observed.

Workup

  1. customwas partitioned between ethyl acetate and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent removed
  5. customto give an oil, which after chromatography (silica, 1% MeOH/EtOAc)

Sources & evidence

ORD record
ord-0bda8040b4a741528c485289d89e4fd1
Source dataset
uspto-grants-2011_03
Patent number
US07902373B2

Reaction notes

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