Ammonium Chloride → HCID 58456398, compound

HRID 1040014Notes

Reaction equation

HRID 1040014 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]([C:24]2[S:28][C:27]([CH:29]3[CH2:34][CH2:33][CH:32]([C:35](O)=[O:36])[CH2:31][CH2:30]3)=[N:26][CH:25]=2)[CH:10]=[C:11]([NH:13][C:14]2[N:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][N:15]=2)[CH:12]=1)=[O:5])[CH3:2].C[N:39](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[Cl-].[NH4+]>C([O-])(O)=O.[Na+].CC1OCCC1>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]([C:24]2[S:28][C:27]([CH:29]3[CH2:34][CH2:33][CH:32]([C:35]([NH2:39])=[O:36])[CH2:31][CH2:30]3)=[N:26][CH:25]=2)[CH:10]=[C:11]([NH:13][C:14]2[N:19]=[C:18]([C:20]([F:21])([F:23])[F:22])[CH:17]=[CH:16][N:15]=2)[CH:12]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67248187HCID 67248187, compound

Product 1

HCID 58456398HCID 58456398, compound

Reagents, catalysts & solvents 2

HCID 73012-MethyltetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The product of Step 1 (396 mg, 0.741 mmol) was dissolved in Mg (3.50 mL). To this solution was added HATU (563 mg, 1.482 mmol) and DIPEA (0.776 mL, 4.44 mmol), followed by ammonium chloride (119 mg, 2.222 mmol). Reaction was complete after stirring 1 hour at room temperature. The reaction mixture was diluted with saturated NaHCO3(aq) and 2-MeTHF. The phases were separated and the organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated to dryness. The mixture of syn and anti iomers was diluted in DMSO was purified by reversed phase HPLC (C18 column; MeCN/water with 0.1% TFA added) to yield:

Workup

  1. customReaction
  2. customThe phases were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. additionThe mixture of syn and anti iomers
  8. additionwas diluted in DMSO
  9. customwas purified by reversed phase HPLC (C18 column; MeCN/water with 0.1% TFA added) to yield

Sources & evidence

ORD record
ord-5d550d22b5f54cd0b4e262fc021eef38
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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