Hydrochloric Acid → HCID 22243979, compound

HRID 890938Notes

Reaction equation

HRID 890938 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:23]([F:24])=[C:22]([F:25])[C:8]2[N:9]([C:14]3[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=3[CH3:21])C[O:11][C:12](=[O:13])[C:7]=2[CH:6]=1)=[O:4].OCC(CO)O.Cl>C1COCC1>[F:24][C:23]1[C:22]([F:25])=[C:8]([NH:9][C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=2[CH3:21])[C:7]([C:12]([OH:13])=[O:11])=[CH:6][C:5]=1[C:3]([NH:2][CH3:1])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 753GlycerolHCID 23598831HCID 23598831, compound

Product 1

HCID 22243979HCID 22243979, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 7,8-difluoro-1-(4-iodo-2-methyl-phenyl)-4-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazine-6-carboxylic acid methylamide in THF (10 mL) is added polymer bound glycerol, (0.33 g, 200–400 mesh) and 10 mL of 1.0 M HCl solution. After stirring for 48 hours at room temperature, the resin is filtered off and the filtrate is transferred to a separatory funnel and partitioned with ethyl acetate. The organics are washed twice with 1.0 M HCl, twice with saturated brine solution, collected, dried over Na2SO4, filtered and concentrated in vacuo affording 4,5-difluoro-6-(-4-iodo-2-methyl-phenylamino)-N-methyl-isophthalamic acid (0.11 g, 76.2%); mp 254–259° C.; 1H NMR (400 MHz; DMSO-d6) 9.31 (s, 1H), 8.19 (s, 1H), 8.07 (d, 1H, J=7.2), 7.56 (s, 1H), 6.69 (t, 1H, J=5.6), 2.74 (d, 3H, J=4.4), 2.20 (s, 3H); MS (APCI)m+1=447; Anal.calcd/found for C16H13F2IN2O3, C 43.07/43.26, H 2.94/3.07. N 6.28/6.10.

Workup

  1. additionis added polymer
  2. filtrationthe resin is filtered off
  3. customthe filtrate is transferred to a separatory funnel
  4. custompartitioned with ethyl acetate
  5. washThe organics are washed twice with 1.0 M HCl, twice with saturated brine solution
  6. customcollected
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-78fa8042770543b6860e64ac596a6830
Source dataset
uspto-grants-2006_02
Patent number
US07001905B2

Reaction notes

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