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Methanol → 3-(5-Ethynylpyridin-3-yl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile trifluoroacetate

HRID 1962754
ノート
印刷プレビュー

反応式

HRID 1962754 の反応式
C[Si](C)(C)CCOC[N:7]1[C:11]2[N:12]=[CH:13][N:14]=[C:15]([C:16]3[CH:17]=[N:18][N:19]([CH:21]([C:25]4[CH:26]=[N:27][CH:28]=[C:29]([C:31]#[C:32][Si](C)(C)C)[CH:30]=4)[CH2:22][C:23]#[N:24])[CH:20]=3)[C:10]=2[CH:9]=[CH:8]1.C(Cl)Cl.[C:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43].[OH-].[K+].CO>>[C:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43].[F:45][C:44]([F:47])([F:46])[C:42]([OH:48])=[O:43].[C:31]([C:29]1[CH:30]=[C:25]([CH:21]([N:19]2[CH:20]=[C:16]([C:15]3[C:10]4[CH:9]=[CH:8][NH:7][C:11]=4[N:12]=[CH:13][N:14]=3)[CH:17]=[N:18]2)[CH2:22][C:23]#[N:24])[CH:26]=[N:27][CH:28]=1)#[CH:32]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 887MethanolHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 57477894HCID 57477894、化合物

生成物 2

HCID 6422Trifluoroacetic acid収率 0.2%
HCID 86632619
3-(5-Ethynylpyridin-3-yl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile trifluoroacetate
収率 36%

実験手順

3-[4-(7-[2-(Trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]-3-{5-[(trimethylsilyl)ethynyl]pyridin-3-yl}propanenitrile (0.050 g, 0.000092 mol) was dissolved in DCM (5.0 mL, 0.078 mol) and TFA (2.0 mL, 0.026 mol). The reaction mixture was stirred at room temperature, for 90 minutes and was concentrated in vacuo. The dry residue dissolved in methanol cooled in an ice bath and a solution of potassium hydroxide (0.482 g, 0.00859 mol) in methanol (10 mL, 0.2 mol) was added. The reaction solution was stirred for 30 min was concentrated and the crude product was purified by preparative HPLC eluting with a water:ACN gradient with 0.2% TFA, to give the title compound as a white amorphous solid (15 mg, 35.85%). LCMS (M+1)+: 340, 1H NMR (400 MHz, DMSO-d6): δ 12.1 (bs, 1H), 9.02 (s, 1H), 8.80 (s, 1H), 8.70 (m, 2H), 8.48 (s, 1H), 8.00 (s, 1H), 7.80 (d, 1H), 7.15 (d, 1H), 6.20 (m, 1H), 4.82 (s, 1H), 3.90 (m, 1H), 3.70 (m, 1H).

後処理

  1. concentrationwas concentrated in vacuo
  2. dissolutionThe dry residue dissolved in methanol
  3. temperaturecooled in an ice bath
  4. stirringThe reaction solution was stirred for 30 min
  5. concentrationwas concentrated
  6. customthe crude product was purified by preparative HPLC
  7. washeluting with a water

出典と根拠

ORDレコード
ord-7950ccbf0d3f4f33becfe1cf6c04743d
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08415362B2

反応ノート

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