Indolin-6-amine → 7-benzyloxy-4-(2,3-dihydro-1H-indol-6-ylamino)-6-methoxy-quinoline-3-carbonitrile

HRID 1595769Notes

Reaction equation

HRID 1595769 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[C:14]([C:19]#[N:20])[CH:15]=[N:16]2)=[CH:11][C:10]=1[O:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:24][C:25]1[CH:33]=[C:32]2[C:28]([CH2:29][CH2:30][NH:31]2)=[CH:27][CH:26]=1.Cl.N1C=CC=CC=1>COCCO>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:24][C:25]3[CH:33]=[C:32]4[C:28]([CH2:29][CH2:30][NH:31]4)=[CH:27][CH:26]=3)=[C:14]([C:19]#[N:20])[CH:15]=[N:16]2)=[CH:11][C:10]=1[O:22][CH3:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 34185Indolin-6-amineHCID 10176127Pyridinium chlorideHCID 224666467-(Benzyloxy)-4-chloro-6-methoxyquinoline-3-carbonitrile

Product 1

HCID 217048177-benzyloxy-4-(2,3-dihydro-1H-indol-6-ylamino)-6-methoxy-quinoline-3-carbonitrileYield 27%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A solution of 586 mg (1.60 mM) of 7-benzyloxy-4-chloro-6-methoxy-quinoline-3-carbonitrile, 560 mg (1.70 mM) of 6-Aminoindolin dihydrchloride salt and 208 mg (1.80 mM) of pyridine hydrochloride in 13 ml of 2-methoxyethanol was refluxed for 3 hours. The reaction was allowed to cool to room temperature and the resulting solid was isolated and washed with excess ethanol and dried under vacuum at 80° C. The resulting solid was digested in 300 ml of ethanol and the volume was reduced to 100 ml. The solid was isolated from the hot solution and the digestion process was repeated a second time. The solid was once again isolated from the hot solution to yield 206 mg of 7-benzyloxy-4-(2,3-dihydro-1H-indol-6-ylamino)-6-methoxy-quinoline-3-carbonitrile as a tan solid.

Workup

  1. customthe resulting solid was isolated
  2. washwashed with excess ethanol
  3. customdried under vacuum at 80° C
  4. customThe solid was isolated from the hot solution
  5. customThe solid was once again isolated from the hot solution

Sources & evidence

ORD record
ord-9f72e12a4af347d5898f3b25ec9aeb4b
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

Loading…