Dimethylformamide → HCID 86730275, compound

HRID 1850221Notes

Reaction equation

HRID 1850221 reaction equation
[CH:1]([CH:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C@H:17]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH3:18])[N:11]=1)([CH3:3])[CH3:2].CN(C(ON1N=N[C:35]2[CH:36]=[CH:37][CH:38]=[N:39][C:34]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN([CH:61]=[O:62])C>ClCCl>[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C@H:17]([CH:19]2[CH2:24][CH2:23][N:22]([C:61]([C:36]3[CH:35]=[CH:34][N:39]=[CH:38][CH:37]=3)=[O:62])[CH2:21][CH2:20]2)[CH3:18])[N:11]=1)([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86730276HCID 86730276, compound

Product 1

HCID 86730275HCID 86730275, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of S)-4-Isopropyl-3-[2-((S)-1-piperidin-4-yl-ethylamino)-pyrimidin-4-yl]-oxazolidin-2-one (20 mg, 0.48 mmol) in dichloromethane (1 mL) and DMF (1 mL) was added HATU (23 mg, 0.06 mmol) and DIPEA (0.03 mL, 0.18 mmol) The reaction was stirred at room temperature for 18 hours. The solvent is then removed under vacuum. The crude material was then purified using reverse phase C18 ODB column water-acetonitrile 0.1% TFA modifier to give (S)-4-Isopropyl-3-(2-{(S)-1-[1-(pyridine-4-carbonyl)-piperidin-4-yl]-ethylamino}-pyrimidin-4-yl)-oxazolidin-2-one (2 mg) in 8% yield.

Workup

  1. customThe solvent is then removed under vacuum
  2. customThe crude material was then purified

Sources & evidence

ORD record
ord-fd9091f117f74fc08bc2c6e4a90221cf
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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