Trifluoroacetic acid → 4-(2,3-dihydro-1H-indol-6-ylamino)-7-hydroxy-6-methoxy-quinoline-3-carbonitrile

HRID 1595770

反応式

HRID 1595770 の反応式
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]1

参加物

3

反応物 2

HCID 6422Trifluoroacetic acidHCID 217048177-benzyloxy-4-(2,3-dihydro-1H-indol-6-ylamino)-6-methoxy-quinoline-3-carbonitrile

生成物 1

HCID 1360184074-(2,3-dihydro-1H-indol-6-ylamino)-7-hydroxy-6-methoxy-quinoline-3-carbonitrile収率 66%

実験手順

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.

後処理

  1. temperaturethe reaction was refluxed for 1.5 h
  2. customThe TFA was removed under vacuum
  3. dissolutionthe resulting film was dissolved in 7 ml of methanol
  4. additionfollowed by the addition of 50 ml of ice cold saturated sodium bicarbonate
  5. customThe resulting solid was isolated
  6. washwashed with excess water
  7. customdried under vacuum at 80° C.

出典と根拠

ORDレコード
ord-498eb7c8ddb24bc1a846dd59fcd427c7
出典データセット
uspto-grants-2001_09
特許番号
US06288082B1

関連ノート

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