Diisopropylethylamine → HCID 71293426, compound

HRID 570891Notes

Reaction equation

HRID 570891 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]2[C:19](=[O:26])[N:20]([CH2:22][C:23](O)=[O:24])[N:21]=[C:8]2[N:7]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)[C:6]=1[CH3:37])=[O:4].[CH:38]([N:41]([CH:44]([CH3:46])C)[CH2:42]C)(C)C.CN(C(ON1N=NC2C=[CH:59][CH:60]=[N:61][C:56]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]2[C:19](=[O:26])[N:20]([CH2:22][C:23](=[O:24])[N:61]([CH2:60][CH2:59][CH2:46][CH2:44][N:41]([CH3:38])[CH3:42])[CH3:56])[N:21]=[C:8]2[N:7]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:34])([F:36])[F:35])[CH:28]=2)[C:6]=1[CH3:37])=[O:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71293468HCID 71293468, compound

Product 1

HCID 71293426HCID 71293426, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Intermediate 17 (50 mg, 0.10 mmol) was dissolved in DMF (1 mL), and diisopropylethylamine (50 μL, 0.29 mmol) and HATU (41 mg, 0.11 mmol) were added. The reaction mixture was stirred at RT for 30 minutes, then N, N, N-trimethylbutanediamine (38 mg, 0.29 mmol) was added, and stirring was continued for a further 18 hours. The reaction mixture was partitioned between EtOAc and water. The organic layer was separated, and the aqueous layer further extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and evaporated in vacuo. The resulting residue was purified by silica gel chromatography eluting with a gradient of 0-10% (2M NH3 in MeOH) in DCM to yield the title compound as a white solid (34 mg).

Workup

  1. stirringstirring
  2. waitwas continued for a further 18 hours
  3. customThe reaction mixture was partitioned between EtOAc and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer further extracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo
  9. customThe resulting residue was purified by silica gel chromatography
  10. washeluting with a gradient of 0-10% (2M NH3 in MeOH) in DCM

Sources & evidence

ORD record
ord-cc0e5795ff264fc39ad0722e85f16507
Source dataset
uspto-grants-2015_05
Patent number
US09023855B2

Reaction notes

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