Ammonium Chloride → HCID 58304040, compound

HRID 1404118Notes

Reaction equation

HRID 1404118 reaction equation
[CH3:1][N:2]([CH3:25])[C:3](=[O:24])[CH2:4][C:5]1[C:13]2[C:8](=[C:9]([F:21])[CH:10]=[C:11]([CH2:16][CH2:17][C:18](O)=[O:19])[C:12]=2[O:14][CH3:15])[N:7]([CH2:22][CH3:23])[CH:6]=1.C[N:27](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+]>C1COCC1.O>[CH3:1][N:2]([CH3:25])[C:3](=[O:24])[CH2:4][C:5]1[C:13]2[C:8](=[C:9]([F:21])[CH:10]=[C:11]([CH2:16][CH2:17][C:18]([NH2:27])=[O:19])[C:12]=2[O:14][CH3:15])[N:7]([CH2:22][CH3:23])[CH:6]=1

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 58303953HCID 58303953, compound

Product 1

HCID 58304040HCID 58304040, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 28-2 (180 mg, 0.51 mmol), HATU (388 mg, 1.02 mmol), DIPEA (220 mg, 1.7 mmol) and ammonium chloride (73 mg, 1.36 mmol) in THF (10 mL) was stirred at room temperature overnight. Water (10 mL) was added, and the reaction mixture was extracted with ethyl acetate (3×20 mL). The combined organic phase was dried over MgSO4, filtered and evaporated to give crude product, which was purified by preparative TLC (petroleum ether/ethyl acetate=1:1) to afford 28-3 (150 mg, 84%) as a yellow solid. LRMS: calc 349.2 and found: 350.0 [M+1].

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (3×20 mL)
  2. dry with materialThe combined organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto give crude product, which
  6. customwas purified by preparative TLC (petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-1a26fa432556486298be59c246428b4f
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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