HCID 22050501, compound → HCID 22050766, compound

HRID 1831993Notes

Reaction equation

HRID 1831993 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[C:14]([CH2:15][N:16]2[C:21]([CH3:22])=[CH:20][C:19]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[F:32])=[C:18]([Cl:33])[C:17]2=[O:34])=[CH:13][N:12]=[C:11]([CH3:35])[N:10]=1>O.CC#N>[ClH:33].[NH2:8][C:9]1[C:14]([CH2:15][N:16]2[C:21]([CH3:22])=[CH:20][C:19]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[F:32])=[C:18]([Cl:33])[C:17]2=[O:34])=[CH:13][N:12]=[C:11]([CH3:35])[N:10]=1

Participants

3

Reactant 1

HCID 22050501HCID 22050501, compound

Product 1

HCID 22050766HCID 22050766, compoundYield 193.6%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Ion exchange (12.5 g) BioRad AG 2×8 resin (200-400 mesh chloride form) was washed with 1M HCl (150 mL), and equilibrated for 2.5 h. This resin was loaded onto a column, and added a solution of EXAMPLE 387 (1.2 g, 2.4 mmol) in water/CH3CN (1:1). The column was eluted slowly over 1 h, fractions were collected, and freeze dried to afford the desired HCl salt (1.03 g, 97%) as a white solid: 1H NMR (CD3OD, 400 Hz) δ 7.60 (m, 2H), 7.04 (m, 2H), 6.64 (s, 1H), 5.31 (s, 2H), 5.17 (s, 2H), 2.50 (s, 3H), 2.47 (s, 3H); ES-HRMS m/z 407.1079 (M+H C19H17N4O2ClF2 requires 407.1081).

Workup

  1. washIon exchange (12.5 g) BioRad AG 2×8 resin (200-400 mesh chloride form) was washed with 1M HCl (150 mL)
  2. washThe column was eluted slowly over 1 h
  3. customfractions were collected
  4. customfreeze dried

Sources & evidence

ORD record
ord-2bd2abcfc8d14700bc4c1e9a4db959c4
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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