Ammonium Chloride → HCID 69929300, compound

HRID 874759Notes

Reaction equation

HRID 874759 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][C:14]2[C:10](=[N:11][N:12]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[C:13]=2[C:16](O)=[O:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[N:29](C(C)C)C(C)C.[Cl-].[NH4+].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[C:16]([C:13]1[N:12]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:24])[CH3:25])[N:11]=[C:10]2[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:15][C:14]=12)(=[O:17])[NH2:29]

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 69929702HCID 69929702, compound

Product 1

HCID 69929300HCID 69929300, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the product obtained in Step C (600 mg, 1.564 mmol) in DMF (15 mL) was added DIPEA (1.366 mL, 7.82 mmol) and ammonium chloride (2.5 g, 46.9 mmol). After stirring for 30 min, HATU (1190 mg, 3.13 mmol) was added. The resulting mixture was stirred at room temperature under nitrogen for 22 h, diluted with ethyl acetate (200 mL), washed with 1N hydrochloric acid (2×100 mL), dried over Na2SO4, filtered and concentrated to give the crude title compound. LC-MS: 383.2 (M+H).

Workup

  1. stirringThe resulting mixture was stirred at room temperature under nitrogen for 22 h
  2. washwashed with 1N hydrochloric acid (2×100 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-54e160f5d2294bc58dc2c671d6ba9dd2
Source dataset
uspto-grants-2015_03
Patent number
US08980929B2

Reaction notes

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