Hydrochloric Acid → 3,5-Difluoro-N-[2-((R)-indan-1-ylamino)-quinolin-5-yl]-benzamide

HRID 2076306Notes

Reaction equation

HRID 2076306 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[N+:21]([O-])=O)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[F:24][C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([F:34])[CH:33]=1)[C:28](Cl)=[O:29].Cl>N1C=CC=CC=1>[F:24][C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([F:34])[CH:33]=1)[C:28]([NH:21][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:18]=1[CH:19]=[CH:20][C:11]([NH:10][C@H:1]1[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH2:2]1)=[N:12]2)=[O:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1456003,5-Difluorobenzoyl chlorideHCID 67096022(R)-Indan-1-yl-(5-nitro-quinolin-2-yl)-amine

Product 1

HCID 670958873,5-Difluoro-N-[2-((R)-indan-1-ylamino)-quinolin-5-yl]-benzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(R)-Indan-1-yl-(5-nitro-quinolin-2-yl)-amine (0.15 g, 0.545 mmol) was dissolved in 1.5 mL pyridine and 3,5-difluorobenzoylchloride (0.98 g, 0.554 mmol) was added. The reaction mixture was stirred at room temperature overnight. 1 N HCl was added until pH5. The mixture was extracted three times with ethyl acetate (50 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The crude product was recrystallized from isopropanol and diisopropylether. The title compound was obtained as a brown solid (44 mg, 19%), MS: m/e=416.3 (M+H+).

Workup

  1. extractionThe mixture was extracted three times with ethyl acetate (50 mL each)
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was recrystallized from isopropanol and diisopropylether

Sources & evidence

ORD record
ord-7e1be38a9ff9420db5494abc05ac442b
Source dataset
uspto-grants-2011_04
Patent number
US07923561B2

Reaction notes

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