HCID 86692237, compound → HCID 86692236, compound

HRID 1469741Notes

Reaction equation

HRID 1469741 reaction equation
COC1C=CC(C[NH:8][C:9]2[C:18]3[C:13](=[C:14]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=4)[CH:15]=[CH:16][CH:17]=3)[N:12]=[CH:11][CH:10]=2)=CC=1>C(O)(C(F)(F)F)=O>[F:29][C:26]([F:27])([F:28])[C:22]1[CH:21]=[C:20]([NH:19][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:13]=2[N:12]=[CH:11][CH:10]=[C:9]3[NH2:8])[CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 1

HCID 86692237HCID 86692237, compound

Product 1

HCID 86692236HCID 86692236, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of N4-(4-methoxybenzyl)-N8-(3-(trifluoromethyl)phenyl)quinoline-4,8-diamine (180 mg, 0.425 mmol) in TFA (2 mL) was stirred at 80° C. for 2 h. Then the reaction mixture was quenched with a saturated solution of NaHCO3 and was extracted with EtOAc. The organic layer was washed with water and brine, separated, dried, filtered and concentrated. The residue was triturated with Et2O to afford 120 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.86 (s, 1H), 8.30 (d, J=4.5 Hz, 1H), 7.66-7.43 (m, 4H), 7.38 (t, J=7.8 Hz, 1H), 7.21-7.18 (d, J=7.8 Hz, 1H), 6.83 (m, 3H), 6.60 (d, J=5.1 Hz, 1H).

Workup

  1. customThen the reaction mixture was quenched with a saturated solution of NaHCO3
  2. extractionwas extracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. customseparated
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-ab8c3479ed614edcb6901cab85815811
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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