Ammonium Chloride → HCID 118071252, compound

HRID 920851Notes

Reaction equation

HRID 920851 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:13]2[CH2:14][O:15][CH2:16][C@@H:12]2[N:11]2[N:17]=[C:18]([I:23])[C:19]([C:20]([OH:22])=O)=[C:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[N:26](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH4+].[Cl-]>CN(C=O)C.O>[C:20]([C:19]1[C:18]([I:23])=[N:17][N:11]2[C@H:12]3[CH2:16][O:15][CH2:14][C@H:13]3[N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:9][C:10]=12)(=[O:22])[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 118061745HCID 118061745, compound

Product 1

HCID 118071252HCID 118071252, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of Intermediate 352E (0.480 g, 1.103 mmol) in DMF (10 mL) at RT was added DIPEA (0.963 mL, 5.51 mmol), HATU (0.839 g, 2.206 mmol), and NH4Cl (0.295 g, 5.51 mmol). After stirring for 12 h, the reaction mixture was diluted with water and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water, dried over Na2SO4 and concentrated to afford Intermediate 352F (0.39 g, 74%) as a pale yellow oil. MS(ES): m/z=435 [M+H]+; 1H NMR (300 MHz, DMSO-d6) δ ppm 7.95 (s, 2H), 5.30-5.13 (m, 2H), 4.86 (dd, J=3.4, 7.6 Hz, 1H), 4.38 (d, J=15.9 Hz, 1H), 4.14-4.03 (m, 1H), 3.98-3.82 (m, 2H), 3.75 (dd, J=6.6, 9.3 Hz, 1H), 1.43 (s, 9H).

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d25c5fd78ee44495af16b669cdeea871
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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