Triphenylphosphine → HCID 90303937、化合物

HRID 62449

反応式

HRID 62449 の反応式
[S:1]([N:11]1[C:19]2[CH2:18][CH2:17][CH2:16][CH:15](O)[C:14]=2[CH:13]=[N:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[Br:21][C:22]1[C:30]2[C:25](=[N:26][CH:27]=[N:28][C:29]=2[NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=2[O:41][CH3:42])[NH:24][N:23]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:21][C:22]1[C:30]2[C:25](=[N:26][CH:27]=[N:28][C:29]=2[NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=2[O:41][CH3:42])[N:24]([CH:15]2[CH2:16][CH2:17][CH2:18][C:19]3[N:11]([S:1]([C:4]4[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=4)(=[O:2])=[O:3])[N:12]=[CH:13][C:14]2=3)[N:23]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 903041681-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-olHCID 178491029HCID 178491029、化合物

生成物 1

HCID 90303937HCID 90303937、化合物収率 32.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-ol (4.05 g, 11.13 mmol), 3-bromo-N-(2,4-dimethoxybenzyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (3.9 g, 13.35 mmol) and PPh3 (4.38 g, 16.70 mmol) in dry THF (110 mL) at 0° C. was added dropwise DIAD (3.37 g, 16.70 mmol) over a period of 5 minutes under a nitrogen atmosphere, then the mixture was stirred at room temperature for 4 hours. Removed the solvent under reduced pressure and then extracted with DCM, the combined organic layer was washed with water, brine and dried over anhydrous Na2SO4. The organic layer was concentrated in vacuo and the residue was purified by preparative HPLC separation to afford 3-bromo-N-(2,4-dimethoxybenzyl)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (2.3 g, yield 32.4%). MS-ESI (m/z): 640 (M+2)+ (Acq Method: 10-80AB_2 min; Rt: 1.357 min)

後処理

  1. customRemoved the solvent under reduced pressure
  2. extractionextracted with DCM
  3. washthe combined organic layer was washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe residue was purified by preparative HPLC separation

出典と根拠

ORDレコード
ord-5ca6649f5c814447b4fbfc149626ab43
出典データセット
uspto-grants-2016_09
特許番号
US09446130B2

関連ノート

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