Ammonium Chloride → HCID 118071203, compound

HRID 920820Notes

Reaction equation

HRID 920820 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]([CH3:14])[CH2:12][N:11]2[N:15]=[C:16]([I:21])[C:17]([C:18](O)=[O:19])=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-].C[N:25](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[C:18]([C:17]1[C:16]([I:21])=[N:15][N:11]2[CH2:12][CH:13]([CH3:14])[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][C:10]=12)(=[O:19])[NH2:25]

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 118060045HCID 118060045, compound

Product 1

HCID 118071203HCID 118071203, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of Intermediate 340E (0.65 g, 1.596 mmol) in DMF (3.0 mL) was added NH4Cl (0.427 g, 7.98 mmol), HATU (1.214 g, 3.19 mmol) and DIPEA (0.836 mL, 4.79 mmol) and the resulting solution was allowed to stir at RT for 3 h. It was diluted with ethyl acetate (10 mL), washed with water, brine, dried over Na2SO4, filtered and the filtrate concentrated. The crude compound was purified by silica gel chromatography (12 g REDISEP® column, eluting with 2% MeOH in CHCl3). Fractions containing the product were combined and evaporated to afford Intermediate 340F as a colorless liquid (0.38 g, 59%). MS(ES): m/z=407 [M+H]+; 1H NMR (300 MHz, DMSO-d6) 8 ppm 6.79-7.56 (m, 2H), 5.01 (d, J=18.51 Hz, 1H), 4.66 (br. s., 1H), 4.39 (d, J=18.13 Hz, 1H), 3.96-4.20 (m, 2H), 1.44 (s, 9H), 1.07 (d, J=6.80 Hz, 3H).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated
  5. customThe crude compound was purified by silica gel chromatography (12 g REDISEP® column, eluting with 2% MeOH in CHCl3)
  6. additionFractions containing the product
  7. customevaporated

Sources & evidence

ORD record
ord-92b2e6da19ae4eabbda5b9b3b4dc17c9
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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