Trifluoroacetic acid → (4-Chloro-benzyl)[5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-pyridin-2-yl]-amine

HRID 1775164ノート

反応式

HRID 1775164 の反応式
C(OC(=O)[N:7]([CH2:35][C:36]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][CH:37]=1)[C:8]1[CH:13]=[CH:12][C:11]([CH:14](O)[C:15]2[C:23]3[CH:22]=[N:21][CH:20]=[N:19][C:18]=3[N:17]([Si](C(C)C)(C(C)C)C(C)C)[CH:16]=2)=[CH:10][N:9]=1)(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([CH2:35][NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]3[C:23]4[CH:22]=[N:21][CH:20]=[N:19][C:18]=4[NH:17][CH:16]=3)=[CH:10][N:9]=2)=[CH:37][CH:38]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57963091(4-chloro-benzyl)-{5-[hydroxy-(7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-pyridin-2-yl}-carbamic acid tert-butyl ester

生成物 1

HCID 44470392(4-Chloro-benzyl)[5-(7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-pyridin-2-yl]-amine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

(4-Chloro-benzyl)-5-[hydroxy-(7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-pyridin-2-yl-carbamic acid tert-butyl ester (43, 0.1 g, 0.16 mmol) was dissolved in 5 mL of acetonitrile and triethylsilane (0.25 mL, 1.6 mmol) was added followed by trifluoroacetic acid (0.12 mL, 1.6 mmol). The reaction was stirred overnight at 80° C., then cooled and concentrated under vacuum. Ethyl acetate was added and the mixture was washed with 1 M potassium carbonate and brine. The organic portion was dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with a gradient of 0-20% methanol in dichloromethane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound, which was further washed with a mixture of ethyl acetate in hexane (P-0001, 0.025 g, 44%). MS (ESI) [M+H+]+=349.9.

後処理

  1. temperaturecooled
  2. concentrationconcentrated under vacuum
  3. additionEthyl acetate was added
  4. washthe mixture was washed with 1 M potassium carbonate and brine
  5. dry with materialThe organic portion was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe resulting material was purified by silica gel column chromatography
  9. washeluting with a gradient of 0-20% methanol in dichloromethane
  10. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-e335b01398a5413e8ecb3fe1a523b9bb
出典データセット
uspto-grants-2016_02
特許番号
US09260437B2

反応ノート

読み込み中…