Trifluoroacetic acid → HCID 89465782、化合物

HRID 1487409

反応式

HRID 1487409 の反応式
FC(F)(F)C(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:22][C:23]1[CH:24]=[C:25]([S:30][C:31]2[CH:32]=[C:33]3[C:39]([NH2:40])=[N:38][NH:37][C:34]3=[N:35][CH:36]=2)[CH:26]=[C:27]([F:29])[CH:28]=1.[CH3:41][N:42]1[CH2:47][CH2:46][N:45]([C:48]2[CH:55]=[CH:54][C:51]([CH:52]=O)=[CH:50][CH:49]=2)[CH2:44][CH2:43]1>O1CCCC1.ClCCl>[F:22][C:23]1[CH:24]=[C:25]([S:30][C:31]2[CH:32]=[C:33]3[C:39]([NH:40][CH2:52][C:51]4[CH:50]=[CH:49][C:48]([N:45]5[CH2:44][CH2:43][N:42]([CH3:41])[CH2:47][CH2:46]5)=[CH:55][CH:54]=4)=[N:38][NH:37][C:34]3=[N:35][CH:36]=2)[CH:26]=[C:27]([F:29])[CH:28]=1

参加物

7

反応物 4

HCID 6422Trifluoroacetic acid2 回HCID 7365334-(4-Methylpiperazin-1-yl)benzaldehydeHCID 5049666Sodium triacetoxyborohydride2 回HCID 178509236HCID 178509236、化合物

生成物 1

HCID 89465782HCID 89465782、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

41.5 μl of trifluoroacetic acid (0.539 mmol) and, in small fractions, 129 mg (0.611 mmol) of sodium triacetoxyborohydride are added to a solution of 100 mg (0.35 mmol) of 5-(3,5-difluorophenylthio)-1H-pyrazolo[3,4-b]pyridin-3-amine and 81 mg (0.395 mmol) of 4-(4-methylpiperazin-1-yl)benzaldehyde in 20 ml of a 1:1 mixture of dichloromethane and tetrahydrofuran. The reaction medium is stirred for 16 hours at room temperature. An additional fraction of 125 μl of trifluoroacetic acid and 388 mg of sodium triacetoxyborohydride are added and the reaction medium is stirred for an additional 24 hours. The solvent is then concentrated and the reaction medium extracted with ethyl acetate and washed using saturated sodium bicarbonate solution. The organic phases are combined, dried on magnesium sulfate and then concentrated to yield a yellow oil. A trituration of this oil in methanol leads to the isolation of 135 mg of a yellow solid.

後処理

  1. stirringthe reaction medium is stirred for an additional 24 hours
  2. concentrationThe solvent is then concentrated
  3. extractionthe reaction medium extracted with ethyl acetate
  4. washwashed
  5. customdried on magnesium sulfate
  6. concentrationconcentrated
  7. customto yield a yellow oil

出典と根拠

ORDレコード
ord-ac14a9ae3b4142e1aa07f635b74d4c56
出典データセット
uspto-grants-2016_08
特許番号
US09428510B2

関連ノート

読み込み中…