Ammonium Chloride → HCID 118071140, compound

HRID 920838Notes

Reaction equation

HRID 920838 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:13]2([CH2:15][CH2:14]2)[CH2:12][N:11]2[N:16]=[C:17]([I:22])[C:18]([C:19]([OH:21])=O)=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-].C[N:26](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.O>[C:19]([C:18]1[C:17]([I:22])=[N:16][N:11]2[CH2:12][C:13]3([CH2:15][CH2:14]3)[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][C:10]=12)(=[O:21])[NH2:26]

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 118061507HCID 118061507, compound

Product 1

HCID 118071140HCID 118071140, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of Intermediate 350E (0.43 g, 1.026 mmol) in DMF (4 mL) was added NH4Cl (0.274 g, 5.13 mmol), HATU (0.780 g, 2.051 mmol) and DIPEA (0.537 mL, 3.08 mmol) and the resulting solution was stirred at RT for 16 h. The reaction mixture was diluted with water (50 mL) and extracted with EtOAc (3×25 mL) The combined organic layer was washed with brine, dried over Na2SO4, filtered and the filtrate concentrated. The residue was triturated with diethyl ether, filtered and dried to afford Intermediate 350F as an off-white solid (0.4 g, 89%). MS(ES): m/z=419 [M+H]+; 1H NMR (400 MHz, chloroform-d) δ ppm 6.56 (br. s., 1H), 5.54 (br. s., 1H), 4.96 (br. s., 2H), 4.04 (br. s., 2H), 1.44 (s, 9H), 1.18 (m, 2H), 0.97-0.84 (m, 2H).

Workup

  1. extractionextracted with EtOAc (3×25 mL) The combined organic layer
  2. washwas washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated
  6. customThe residue was triturated with diethyl ether
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-d2342f14741e4a1c8ff8df7a5e233bc6
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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