Ethylenediamine → 3-(benzyloxy)-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutylacetonitrile

HRID 1692960ノート

反応式

HRID 1692960 の反応式
[CH2:1]([O:8][CH:9]1[CH2:12][C:11]([CH2:35][C:36]#[N:37])([N:13]2[CH:17]=[C:16]([C:18]3[C:19]4[CH:26]=[CH:25][N:24](COCC[Si](C)(C)C)[C:20]=4[N:21]=[CH:22][N:23]=3)[CH:15]=[N:14]2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(N)CN>>[CH2:1]([O:8][CH:9]1[CH2:12][C:11]([CH2:35][C:36]#[N:37])([N:13]2[CH:17]=[C:16]([C:18]3[C:19]4[CH:26]=[CH:25][NH:24][C:20]=4[N:21]=[CH:22][N:23]=3)[CH:15]=[N:14]2)[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 670171953-(benzyloxy)-1-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutylacetonitrile

生成物 1

HCID 442322293-(benzyloxy)-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutylacetonitrile

実験手順

3-(Benzyloxy)-1-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutylacetonitrile (0.024 g, 0.000046 mol) was treated with trifluoroacetic acid (0.5 mL, 0.006 mol) at rt for 30 min, then evaporated to dry. The residue was dissolved in MeOH (1 mL) and treated with ethylenediamine (0.2 mL, 0.003 mol) at rt for 2 h. The reaction mixture was concentrated in vacuo and the resulting residue purified on prep. HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.15% NH4OH) to give 2 isomers of the desired products. First peak retention time 1.406 min; LCMS calculated for C22H21N6O(M+H)+: 385.2; Found: 385.3. 1H NMR (400 MHz, DMSO-d6): δ 12.10 (1H, br s), 8.71 (1H, s), 8.67 (1H, s), 8.38 (1H, s), 7.58 (1H, d, J=3.6 Hz), 7.33 (4H, m), 7.29 (1H, m), 7.05 (1H, d, J=3.6 Hz), 4.43 (2H, s), 4.23 (1H, m), 3.43 (2H, s), 2.78 (2H, m), 2.74 (2H, m) ppm. Second peak retention time 1.474 min, LCMS calculated for C22H21N6)(M+H)+: 385.2; Found: 385.3. 1H NMR (400 MHz, DMSO-d6): δ 12.10 (1H, br s), 8.79 (1H, s), 8.67 (1H, s), 8.39 (1H, s), 7.59 (1H, d, J=3.6 Hz), 7.34 (4H, m), 7.29 (1H, m), 7.06 (1H, d, J=3.6 Hz), 4.44 (2H, s), 4.14 (1H, m), 3.44 (2H, s), 3.16 (2H, m), 2.44 (2H, m) ppm.

後処理

  1. customevaporated
  2. customto dry
  3. dissolutionThe residue was dissolved in MeOH (1 mL)
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthe resulting residue purified on prep
  6. washHPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.15% NH4OH)

出典と根拠

ORDレコード
ord-349d8a0f87c84a1c8d95029b7886aabe
出典データセット
uspto-grants-2012_04
特許番号
US08158616B2

反応ノート

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