Ethylenediamine → N2-{5-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyridin-3-yl}-N-(2,2,2-trifluoroethyl)valinamide

HRID 510213ノート

反応式

HRID 510213 の反応式
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]3[C:15]([C:16]4[CH:17]=[C:18]([NH:22][C@H:23]([C:27]([NH:29][CH2:30][C:31]([F:34])([F:33])[F:32])=[O:28])[CH:24]([CH3:26])[CH3:25])[CH:19]=[N:20][CH:21]=4)=[CH:14][N:13](COCC[Si](C)(C)C)[C:10]3=[N:11][CH:12]=2)[CH:4]=[N:3]1.C(O)(C(F)(F)F)=O.C(N)CN.[OH-].[Na+]>C(Cl)Cl.CS(C)=O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]3[C:15]([C:16]4[CH:17]=[C:18]([NH:22][C@H:23]([C:27]([NH:29][CH2:30][C:31]([F:32])([F:33])[F:34])=[O:28])[CH:24]([CH3:26])[CH3:25])[CH:19]=[N:20][CH:21]=4)=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH:4]=[N:3]1

参加物

7

反応物 4

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 131733262N2-{5-[5-(1-methyl-1H-pyrazol-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-3-yl]pyridin-3-yl}-N-(2,2,2-trifluoroethyl)valinamide

生成物 1

HCID 89488610N2-{5-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyridin-3-yl}-N-(2,2,2-trifluoroethyl)valinamide

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution N2-{5-[5-(1-methyl-1H-pyrazol-4-yl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-3-yl]pyridin-3-yl}-N-(2,2,2-trifluoroethyl)valinamide 8-1a (190 mg, 0.316 mmol) from step 1 in DCM (2 mL) was added TFA (2.4 mL, 31.6 mmol) and the resultant mixture was stirred for 2 h. The mixture was concentrated in vacuo, resuspended in MeOH (1 mL) and to this was added ethylenediamine (0.043 mL, 0.632 mmol) and sodium hydroxide (10 M aq) (0.221 mL, 2.21 mmol). After 18 h, the reaction was transferred to vial with an additional 1 mL of dimethylsulfoxide and this solution was purified by mass triggered reverse phase HLPC. The fractions containing product 8-1 were basified with NaHCO3, dried over MgSO4, filtered and concentrated.

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. customthis solution was purified by mass triggered reverse phase HLPC
  3. additionThe fractions containing product 8-1
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-cfc4de8653204347aaabdb837a0aa013
出典データセット
uspto-grants-2015_08
特許番号
US09096598B2

反応ノート

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