Diisopropylethylamine → HCID 71293422, compound

HRID 2362320Notes

Reaction equation

HRID 2362320 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C@@H: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]([OH:25])=O)[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=NC2[CH:58]=[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[C@@H:10]([C:11]2[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=2)[N:9]2[C:19](=[O:26])[N:20]([CH2:22][C:23](=[O:25])[N:61]([CH2:60][CH2:59][CH2:58][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:35])[F:36])[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 71293493HCID 71293493, compound

Product 1

HCID 71293422HCID 71293422, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Intermediate 26 (250 mg, 0.46 mmol) was dissolved in DMF (5 mL), and then diisopropylethylamine (240 μL, 1.4 mmol) and HATU (266 mg, 0.7 mmol) were added. The reaction mixture was stirred at RT for 40 minutes, then N,N,N-trimethylpentanediamine (288 mg, 2.0 mmol) in DMF (1 mL) 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 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 4-8% (2 M NH3 in MeOH) in DCM followed by a gradient of 6-7% (2 M NH3 in MeOH) in DCM. The resulting residue was purified by MDAP to yield the title compound as an off-white solid (88 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 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 4-8% (2 M NH3 in MeOH) in DCM
  11. customThe resulting residue was purified by MDAP

Sources & evidence

ORD record
ord-ddf20099576f431c88132262c360da9c
Source dataset
uspto-grants-2014_04
Patent number
US08691826B2

Reaction notes

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