Trifluoroacetic acid → 5-(2-Benzyl-2H-indazol-6-yl)-7-(3-piperazin-1-yl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine

HRID 1972802ノート

反応式

HRID 1972802 の反応式
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[N:28]4[C:23]([C:24]([NH2:29])=[N:25][CH:26]=[N:27]4)=[C:22]([C:30]4[CH:31]=[CH:32][C:33]5[C:37]([CH:38]=4)=[N:36][N:35]([CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[CH:34]=5)[CH:21]=3)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:39]([N:35]1[CH:34]=[C:33]2[C:37]([CH:38]=[C:30]([C:22]3[CH:21]=[C:20]([C:16]4[CH:17]=[CH:18][CH:19]=[C:14]([N:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)[CH:15]=4)[N:28]4[C:23]=3[C:24]([NH2:29])=[N:25][CH:26]=[N:27]4)[CH:31]=[CH:32]2)=[N:36]1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 585292904-{3-[4-Amino-5-(2-benzyl-2H-indazol-6-yl)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 585293825-(2-Benzyl-2H-indazol-6-yl)-7-(3-piperazin-1-yl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-4-ylamine収率 30%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The product from step 5 (55 mg, (0.09 mmol) was dissolved in 1 mL of CH2Cl2 and 1 mL of TFA was added dropwise. The mixture stirred for 1 hour and then concentrated to dryness. The residue was dissolved in acetonitrile and water was added and the pH was adjusted to 9 by the addition of aqueous K3PO4. The mixture was concentrated in vacuo and the solids obtained were extracted with MeOH, and then concentrated in vacuo again. The solid residue obtained was re-extracted with MeOH, filtered and the filtrate purified by preparative HPLC to provide 14 mg (30%) of the title compound. 1H-NMR (DMSO-d6) 8.35 (s, 1H), 7.61 (s, 1H), 7.58 (bs, 2H), 7.39-7.24 (m, 7H), 7.22 (s, 1H), 7.11-7.01, (m, 2H), 6.77 (d, 1H), 6.57 (d, 1H), 6.26 (d, 1H), 5.57 (s, 2H), 3.10 (m, 4H), 2.84 (m, 4H); LC-MS [M+H]+=501.2, RT=2.24 min.

後処理

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in acetonitrile
  3. additionwater was added
  4. additionthe pH was adjusted to 9 by the addition of aqueous K3PO4
  5. concentrationThe mixture was concentrated in vacuo
  6. customthe solids obtained
  7. extractionwere extracted with MeOH
  8. concentrationconcentrated in vacuo again
  9. customThe solid residue obtained
  10. extractionwas re-extracted with MeOH
  11. filtrationfiltered
  12. customthe filtrate purified by preparative HPLC

出典と根拠

ORDレコード
ord-61942e22b980407e8479b62daf0517b3
出典データセット
uspto-grants-2013_04
特許番号
US08431695B2

反応ノート

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