Hydrochloric Acid → HCID 10056005, compound

HRID 585040Notes

Reaction equation

HRID 585040 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1C#N.C[CH2:22][N:23](CC)CC.[C:28]12[C:42](=[O:43])[O:41][S:38](=[O:40])(=[O:39])[C:29]=1[C:30]([Br:37])=[C:31]([Br:36])[C:32]([Br:35])=[C:33]2[Br:34].Cl>C1COCC1>[Br:37][C:30]1[C:31]([Br:36])=[C:32]([Br:35])[C:33]([Br:34])=[C:28]([C:42]([NH:1][C:2]2[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=2[NH:12][C:13]2[CH:20]=[CH:19][C:18]([C:22]#[N:23])=[CH:17][CH:14]=2)=[O:43])[C:29]=1[S:38]([OH:41])(=[O:40])=[O:39]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 1103353H-2,1-Benzoxathiol-3-one, 4,5,6,7-tetrabromo-, 1,1-dioxideHCID 22339364HCID 22339364, compound

Product 1

HCID 10056005HCID 10056005, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Into a mL are placed -{[2-amino-4-(trifluoromethyl)phenyl]amino}benzonitrile (100 mg, 0.361 mmol), Et3N (0.15 mL, 1.08 mmol), tetrabromo-2-sulfobenzoic acid cyclic anhydride (270 mg, 0.541 mmol), and THF (5 mL). The mixture is heated with efficient shaking at 40° C. for 16 h. The solution is cooled and 1M HCl is added and the organic phase is extracted with EtOAc (3×). The organic fractions are combined, washed with brine, and concentrated. The crude product is dissolved in MeOH (20 mL) and then Dowex (10 eq) is added. The mixture is efficiently shaken at rt for 16 h. The resin is then filtered and the solution concentrated. The yield is 108 mg of 2,3,4,5-tetrabromo-6-({[2-[(4-cyanophenyl)amino]-5-(trifluoromethyl)phenyl]amino}carbonyl)benzenesulfonic acid, 46%. 1H NMR (400 MHz, DMSO-d6): □ 10.06 (s, 1 H), 8.89 (s, 1 H), 7.70-7.68 (m, 2 H), 7.65-7.61 (m, 2 H), 7.56-7.54 (m, 1 H), 7.32-7.30 (m, 2 H). ESI+ for C21H10Br4F3N3O4S m/z 778 (M+H)+.

Workup

  1. temperatureThe mixture is heated
  2. temperatureThe solution is cooled
  3. extractionthe organic phase is extracted with EtOAc (3×)
  4. washwashed with brine
  5. concentrationconcentrated
  6. dissolutionThe crude product is dissolved in MeOH (20 mL)
  7. additionDowex (10 eq) is added
  8. stirringThe mixture is efficiently shaken at rt for 16 h
  9. filtrationThe resin is then filtered
  10. concentrationthe solution concentrated

Sources & evidence

ORD record
ord-825c155076c34d4d98fbf4958b70e0e2
Source dataset
uspto-grants-2005_08
Patent number
US06930106B2

Reaction notes

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