Dimethylformamide → HCID 67381444, compound

HRID 2237380Notes

Reaction equation

HRID 2237380 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:15]([OH:17])=O)[CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:19]1[CH2:24][CH2:23][O:22][CH2:21]C1.CN(C(O[N:33]1N=N[C:35]2C=CC=N[C:34]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CO[C:51]([CH3:54])([CH3:53])[CH3:52].CN(C=[O:59])C>>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:15]([NH:19][C@H:24]([C:23]([O:22][CH3:21])=[O:59])[CH2:52][C:51]1[CH:54]=[N:33][CH:34]=[CH:35][CH:53]=1)=[O:17])[CH2:10][Si:11]([CH3:12])([CH3:13])[CH3:14])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 15413tert-Butyl methyl etherHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 14499069HCID 14499069, compound

Product 1

HCID 67381444HCID 67381444, compound

Procedure

The compound from example 87A (10.31 g, 39.4 mmol) and the compound from example 71A (16.10 g, 39.4 mmol, 1 equivalent) are dissolved at 0° C. in DMF (186 ml). NMM (17.34 ml, 16.00 g, 4 equivalents) and HATU (22.49 g, 59.16 mmol, 1.5 equivalents) are then added. The mixture is stirred at RT for 2 hours. tert-Butyl methyl ether is added to the mixture and the mixture is washed with a saturated sodium carbonate solution. The aqueous phase is reextracted once with tert-butyl methyl ether, and the combined organic phases are then washed with 1 M aqueous citric acid and once again with a saturated sodium carbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo. The mixture is filtered through silica gel (cyclohexane/ethyl acetate 2:1). Yield: 14.1 g (84% of theory).

Workup

  1. washthe mixture is washed with a saturated sodium carbonate solution
  2. washthe combined organic phases are then washed with 1 M aqueous citric acid and once again with a saturated sodium carbonate solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationThe mixture is filtered through silica gel (cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-ecc67e8280ef449fbfb86912cd7c3f1e
Source dataset
uspto-grants-2010_05
Patent number
US07718611B2

Reaction notes

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