Dimethylformamide → HCID 63750403, compound

HRID 706334Notes

Reaction equation

HRID 706334 reaction equation
CN(C(ON1N=N[C:11]2[CH:12]=CC=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CC[N:27]([CH:31]([CH3:33])C)[CH:28]([CH3:30])[CH3:29].CNC[CH2:37][OH:38].[CH3:39][N:40]([CH:42]=[O:43])[CH3:41]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[OH:38][CH2:37][CH2:39][N:40]([CH3:41])[C:42]([C:11]1[CH:10]=[C:30]2[C:28](=[CH:29][CH:12]=1)[NH:27][CH:31]=[CH:33]2)=[O:43]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 80162-(Methylamino)ethanolHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 63750403HCID 63750403, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of R-5 (100 mg, 0.62 mmol) in anhydrous DMF (3 mL) is added HATU (472 mg, 1.24 mmol) and DIPEA (322 mL, 1.86 mmol) and the reaction is stirred at room temperature for 1 h. 2-(Methylamino)ethanol (100 mL, 1.24 mmol) is added and the mixture is stirred at room temperature for 16 h. The reaction is diluted with DCM and saturated aqueous NaHCO3, the layers separated, and the aqueous solution extracted with further DCM. Combined organics are washed with saturated aqueous NaHCO3, and brine. NaCl is then added to the combined aqueous phases and then the aqueous solution extracted with EtOAc. Combined organics are washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give the title intermediate I-6 (379.4 mg) m/z 219.0 [M+H].

Workup

  1. stirringthe mixture is stirred at room temperature for 16 h
  2. customthe layers separated
  3. extractionthe aqueous solution extracted with further DCM
  4. washCombined organics are washed with saturated aqueous NaHCO3, and brine
  5. additionNaCl is then added to the combined aqueous phases
  6. extractionthe aqueous solution extracted with EtOAc
  7. washCombined organics are washed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ec61f65abe884bb88e9e9ba76a31e107
Source dataset
uspto-grants-2015_11
Patent number
US09174980B2

Reaction notes

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