Hydrochloric Acid → HCID 90413897, compound

HRID 1776729Notes

Reaction equation

HRID 1776729 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:17])[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1.[C:18]1(=[O:28])[C@@H:26]2[C@@H:21]([CH2:22][CH2:23][CH2:24][CH2:25]2)[C:20](=O)[O:19]1.Cl.C([O-])(O)=O.[Na+]>C(#N)C>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:8]2[C:7]3[CH:6]=[CH:5][C:4]([OH:17])=[CH:3][C:2]=3[N:1]=[C:20]2[C@H:21]2[CH2:22][CH2:23][CH2:24][CH2:25][C@H:26]2[C:18]([OH:28])=[O:19])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 641660Hexahydrophthalic anhydride, cis-HCID 90415269HCID 90415269, compound

Product 1

HCID 90413897HCID 90413897, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

3-Amino-4-((4-bromobenzyl)amino)phenol (7.8 g, 27 mmol) and cis-hexahydroisobenzofuran-1,3-dione (4.1 g, 27 mmol) were dissolved in acetonitrile (200 mL) and the mixture heated to 80° C. After 18 h, HCl (50 mL, 6 N) was added and the resulting mixture stirred at 60° C. for 16 h. The mixture was then cooled to RT and the pH was adjusted to ˜pH 7 with sat.NaHCO3. The aqueous was then extracted with EtOAc (3×200 mL). The combined organics were washed with water (200 mL), dried with Na2SO4, filtered and concentrated to dryness. The residue was purified by FCC to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ 12.13 (s, 1H), 8.93 (s, 1H), 7.47 (d, J=8.4, 2H), 7.06 (dd, J=8.6, 2.7, 3H), 6.89 (d, J=2.1, 1H), 6.60 (dd, J=8.6, 2.2, 1H), 5.52-5.26 (m, 2H), 3.63 (d, J=4.4, 1H), 2.70 (d, J=10.7, 1H), 2.55 (d, J=8.9, 1H), 1.81 (d, J=8.9, 2H), 1.61 (dd, J=32.5, 21.3, 3H), 1.34 (s, 2H).

Workup

  1. temperatureThe mixture was then cooled to RT
  2. extractionThe aqueous was then extracted with EtOAc (3×200 mL)
  3. washThe combined organics were washed with water (200 mL)
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-9267cc8016654b55909091ea22613793
Source dataset
uspto-grants-2016_02
Patent number
US09265770B2

Reaction notes

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