Trifluoroacetic acid → 4-(2,3-dihydro-1H-indol-6-ylamino)-7-hydroxy-6-methoxy-quinoline-3-carbonitrile
Reaction equation
FC(F)(F)C(O)=O.C([O:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([NH:28][C:29]3[CH:37]=[C:36]4[C:32]([CH2:33][CH2:34][NH:35]4)=[CH:31][CH:30]=3)=[C:21]([C:26]#[N:27])[CH:22]=[N:23]2)=[CH:18][C:17]=1[O:38][CH3:39])C1C=CC=CC=1>>[NH:35]1[C:36]2[C:32](=[CH:31][CH:30]=[C:29]([NH:28][C:20]3[C:19]4[C:24](=[CH:25][C:16]([OH:15])=[C:17]([O:38][CH3:39])[CH:18]=4)[N:23]=[CH:22][C:21]=3[C:26]#[N:27])[CH:37]=2)[CH2:33][CH2:34]1Participants
3
Procedure
To 5 ml of trifluoroacetic acid was added 206 mg 7-benzyloxy-4-(2,3-dihydro-1H-indol-6-ylamino)-6-methoxy-quinoline-3-carbonitrile and the reaction was refluxed for 1.5 h. The TFA was removed under vacuum and the resulting film was dissolved in 7 ml of methanol followed by the addition of 50 ml of ice cold saturated sodium bicarbonate. The solution was allowed to stand at 10° C. for 1 h. The resulting solid was isolated, washed with excess water and dried under vacuum at 80° C. to yield 107 mg of 4-(2,3-dihydro-1H-indol-6-ylamino)-7-hydroxy-6-methoxy-quinoline-3-carbonitrile. This compound was taken directly on to the next step without purification.
Workup
- temperaturethe reaction was refluxed for 1.5 h
- customThe TFA was removed under vacuum
- dissolutionthe resulting film was dissolved in 7 ml of methanol
- additionfollowed by the addition of 50 ml of ice cold saturated sodium bicarbonate
- customThe resulting solid was isolated
- washwashed with excess water
- customdried under vacuum at 80° C.
Sources & evidence
- ORD record
- ord-498eb7c8ddb24bc1a846dd59fcd427c7
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06288082B1
Reaction notes
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