Trifluoroacetic acid → N-[[(2S)-1-benzylpyrrolidin-2-yl]methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide

HRID 589982ノート

反応式

HRID 589982 の反応式
[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][N:14](C(OC(C)(C)C)=O)[S:15]([N:18]1[C:23]2([CH2:25][CH2:24]2)[CH2:22][N:21]([C:26]2[C:27]3[CH:34]=[CH:33][N:32](C(OC(C)(C)C)=O)[C:28]=3[N:29]=[CH:30][N:31]=2)[CH2:20][CH2:19]1)(=[O:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:14][S:15]([N:18]1[C:23]2([CH2:24][CH2:25]2)[CH2:22][N:21]([C:26]2[C:27]3[CH:34]=[CH:33][NH:32][C:28]=3[N:29]=[CH:30][N:31]=2)[CH2:20][CH2:19]1)(=[O:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 68296033tert-butyl 4-[8-[[(2S)-1-benzylpyrrolidin-2-yl]methyl-tert-butoxycarbonyl-sulfamoyl]-5,8-diazaspiro[2.5]octan-5-yl]pyrrolo[2,3-d]pyrimidine-7-carboxylate2 回

生成物 1

HCID 57411876N-[[(2S)-1-benzylpyrrolidin-2-yl]methyl]-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

tert-butyl 4-[8-[[(2S)-1-benzylpyrrolidin-2-yl]methyl-tert-butoxycarbonyl-sulfamoyl]-5,8-diazaspiro[2.5]octan-5-yl]pyrrolo[2,3-d]pyrimidine-7-carboxylate (Intermediate 48) (0.57 mmol) was dissolved in DCM (10 mL) and added TFA (1 mL). The reaction mixture was stirred at rt for 16 h, then added NaHCO3 (15 mL) and extracted with EtOAc (2×25 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by flash chromatography on silica using EtOAc and MeOH in heptane as eluent.

後処理

  1. extractionadded NaHCO3 (15 mL) and extracted with EtOAc (2×25 mL)
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by flash chromatography on silica

出典と根拠

ORDレコード
ord-75bd5104d5b142e58c413a13002aafd9
出典データセット
uspto-grants-2016_01
特許番号
US09233964B2

反応ノート

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