Trifluoroacetic acid → HCID 89465782, 화합물

HRID 1487409

반응식

HRID 1487409 반응식
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

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acid2회HCID 7365334-(4-Methylpiperazin-1-yl)benzaldehydeHCID 5049666Sodium triacetoxyborohydride2회HCID 178509236HCID 178509236, 화합물

생성물 1

HCID 89465782HCID 89465782, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ac14a9ae3b4142e1aa07f635b74d4c56
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428510B2

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