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Trifluoroacetic acid → HCID 46244494, 화합물

HRID 1803852
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HRID 1803852 반응식
[NH2:1][C:2]1[CH:29]=[C:28]([N:30]([CH2:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])[CH3:31])[CH:27]=[CH:26][C:3]=1[C:4]([NH:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH2:17][C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=3)[CH:14]=2)[NH:9][N:8]=1)=[O:5].[O:38]1[CH2:43][CH2:42][C:41](=O)[CH2:40][CH2:39]1.C(O)(C(F)(F)F)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C[N+](C)(C)C>C(Cl)Cl>[F:24][C:22]1[CH:23]=[C:18]([CH:19]=[C:20]([F:25])[CH:21]=1)[CH2:17][O:16][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[NH:6][C:4](=[O:5])[C:3]1[CH:26]=[CH:27][C:28]([N:30]([CH2:32][CH2:33][CH2:34][N:35]([CH3:36])[CH3:37])[CH3:31])=[CH:29][C:2]=1[NH:1][CH:41]1[CH2:42][CH2:43][O:38][CH2:39][CH2:40]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 46244400HCID 46244400, 화합물

생성물 1

HCID 46244494HCID 46244494, 화합물수율 46.5%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

2-Amino-N-[5-(3,5-difluoro-benzyloxy)-1H-indazol-3-yl]-4-[(3-dimethylamino-propyl)-methyl-amino]-benzamide (150 mg, 0.29 mmol) in DCM (4 mL) was treated, at 4° C., under a nitrogen atmosphere, with tetrahydro-4H-pyran-4-one (0.34 mL, 0.37 mmol), TFA (0.23 mL, 2.95 mmol) and finally with tetramethylammonium triacetoxyborohydride ((204 mg, 0.74 mmol). After 1.5 hours DCM, was added (25 mL) and the organic layer was washed with water (25 mL), saturated NaHCO3 solution (25 mL) and brine. After drying over anhydrous sodium sulfate, removal of the solvent and purification of the crude over silica gel (DCM: 7N NH3 in MeOH 9:1), 80 mg of title compound were obtained in 46% yield.

후처리

  1. additionwas added (25 mL)
  2. washthe organic layer was washed with water (25 mL), saturated NaHCO3 solution (25 mL) and brine
  3. dry with materialAfter drying over anhydrous sodium sulfate, removal of the solvent and purification of the crude over silica gel (DCM: 7N NH3 in MeOH 9:1)

출처 및 근거

ORD 기록
ord-9e154a28d7094433988c9965663bf759
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08354399B2

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