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Trifluoroacetic acid → N-[1-{[3-(Aminomethyl)phenyl]methyl}-5-fluoro-4-(methyloxy)-1H-indazol-3-yl]-5-chloro-2-thiophenesulfonamide

HRID 1892931
ノート
印刷プレビュー

反応式

HRID 1892931 の反応式
CC([N:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][N:17]2[C:25]3[C:20](=[C:21]([O:27][CH3:28])[C:22]([F:26])=[CH:23][CH:24]=3)[C:19]([NH:29][S:30]([C:33]3[S:34][C:35]([Cl:38])=[CH:36][CH:37]=3)(=[O:32])=[O:31])=[N:18]2)[CH:11]=1)C(=O)[O-])(C)C.FC(F)(F)C(O)=O>ClCCl.CO.CS(C)=O>[NH2:5][CH2:9][C:10]1[CH:11]=[C:12]([CH2:16][N:17]2[C:25]3[C:20](=[C:21]([O:27][CH3:28])[C:22]([F:26])=[CH:23][CH:24]=3)[C:19]([NH:29][S:30]([C:33]3[S:34][C:35]([Cl:38])=[CH:36][CH:37]=3)(=[O:32])=[O:31])=[N:18]2)[CH:13]=[CH:14][CH:15]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 6422Trifluoroacetic acidHCID 86644812HCID 86644812、化合物

生成物 1

HCID 59455989N-[1-{[3-(Aminomethyl)phenyl]methyl}-5-fluoro-4-(methyloxy)-1H-indazol-3-yl]-5-chloro-2-thiophenesulfonamide収率 45%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 887Methanol溶媒2 回
HCID 6344
Dichloromethane
溶媒

実験手順

1,1-Dimethylethyl[(3-{[3-{[(5-chloro-2-thienyl)sulfonyl]amino}-5-fluoro-4-(methyloxy)-1H-indazol-1-yl]methyl}phenyl)methyl]carbamate (for a preparation see Intermediate 60) (2.7 g, 4.65 mmol) was dissolved in dichloromethane (20 mL). Trifluoroacetic acid (5.00 mL) was added to the reaction and stirred for 1 h. The reaction mixture was concentrated in vacuo to leave a purple residue. The residue was dissolved in methanol and loaded onto a methanol pre-conditioned SCX-2 ion-exchange cartridge (70 g). The cartridge was washed well with methanol, followed by HCl in methanol, then methanol and finally ammonia in methanol. Fractions were combined and evaporated in vacuo to give an off white solid, which was dissolved in DMSO, filtered and loaded onto a methanol pre-conditioned SCX-2 ion-exchange cartridge (70 g). The cartridge was washed well with Methanol followed by 2M ammonia in methanol. Evaporation of the solvent from the ammoniacal fractions gave the title compound (1 g, 45%) as a white solid: LCMS (System A) RT=0.84 min, ES+ve m/z 481/483 (M+H)+.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto leave a purple residue
  3. washThe cartridge was washed well with methanol
  4. customevaporated in vacuo
  5. customto give an off white solid, which
  6. filtrationfiltered
  7. washThe cartridge was washed well with Methanol
  8. customEvaporation of the solvent from the ammoniacal fractions

出典と根拠

ORDレコード
ord-6aebe84a51bc4f1bbcb6851350d15706
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08507543B2

反応ノート

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