3-Chloro-5-{[5-chloro-1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-1H-indazol-4-yl]oxy}benzonitrile → HCID 178509921、化合物

HRID 505511ノート

反応式

HRID 505511 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][N:15]3[CH2:21][C:22]2[C:30]3[C:25](=[N:26][C:27]([NH:31]CC4C=CC(OC)=CC=4)=[CH:28][CH:29]=3)[N:24](CC3C=CC(OC)=CC=3)[N:23]=2)[CH:9]=1)[C:5]#[N:6]>C(O)(C(F)(F)F)=O>[NH2:31][C:27]1[N:26]=[C:25]2[NH:24][N:23]=[C:22]([CH2:21][N:15]3[C:16]4[C:12](=[C:11]([O:10][C:8]5[CH:7]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:9]=5)[C:5]#[N:6])[C:19]([Cl:20])=[CH:18][CH:17]=4)[CH:13]=[N:14]3)[C:30]2=[CH:29][CH:28]=1

参加物

3

反応物 1

HCID 568338523-Chloro-5-{[5-chloro-1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-1H-indazol-4-yl]oxy}benzonitrile

生成物 1

HCID 178509921HCID 178509921、化合物

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

3-chloro-5-{[5-chloro-1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-1H-indazol-4-yl]oxy}benzonitrile (0.848 g, 1.228 mmol) was dissolved in TFA (10 mL) and placed in an oil bath at 75° C. After 2.5 hours, the reaction mixture was allowed to cool to room temperature and was concentrated under reduced pressure. The resulting residue was suspended in a chloroform and ethyl acetate mixture (4:1, 200 mL) and aqueous sodium bicarbonate (50 mL) was added. Ethyl acetate was then added until both phases had become solutions. The organic phase was separated and the aqueous phase was washed with chloroform (2×100 mL). The combined organic fractions were dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was subjected to automated silica gel chromatography eluting with a gradient of 0-10% methanol in chloroform to yield the title product. 1H NMR (DMSO-d6): δ 12.60 (s, 1H), 7.86 (s, 1H), 7.81-7.78 (m, 1H), 7.73 (d, J=9.0 Hz, 1H), 7.58 (d, J=9.0 Hz, 1H), 7.49-7.47 (m, 1H), 7.38-7.34 (m, 2H), 6.30 (s, 2H), 6.21 (d, J=8.8 Hz, 1H), 5.82 (s, 2H). LRMS (M+1)=449.7

後処理

  1. customplaced in an oil bath at 75° C
  2. concentrationwas concentrated under reduced pressure
  3. additionwas added
  4. additionEthyl acetate was then added until both phases
  5. customThe organic phase was separated
  6. washthe aqueous phase was washed with chloroform (2×100 mL)
  7. dry with materialThe combined organic fractions were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. washeluting with a gradient of 0-10% methanol in chloroform

出典と根拠

ORDレコード
ord-d130ee69827644d7bb4bda1c4c5aac82
出典データセット
uspto-grants-2010_08
特許番号
US07781454B2

反応ノート

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