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Trifluoroacetic acid → HCID 178507870、化合物

HRID 1529457
ノート
印刷プレビュー

反応式

HRID 1529457 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[C:14]([C:27]3[N:32]=[C:31](S(C)(=O)=O)[N:30]=[C:29]([N:37]4[CH2:42][CH2:41][CH:40]([NH:43]C(=O)OC(C)(C)C)[CH2:39][CH2:38]4)[CH:28]=3)=[CH:15][N:16](S(C3C=CC(C)=CC=3)(=O)=O)[C:11]2=[CH:10][CH:9]=1.[OH-].[Na+].C(O)(C(F)(F)F)=[O:54]>O1CCOCC1.C(Cl)(Cl)Cl.CC(O)C>[NH2:43][CH:40]1[CH2:39][CH2:38][N:37]([C:29]2[CH:28]=[C:27]([C:14]3[C:12]4=[N:13][C:8]([C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=5[F:1])=[CH:9][CH:10]=[C:11]4[NH:16][CH:15]=3)[N:32]=[C:31]([OH:54])[N:30]=2)[CH2:42][CH2:41]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6422Trifluoroacetic acid2 回HCID 14798Sodium HydroxideHCID 67959655tert-butyl 1-(6-(5-(2-fluorophenyl)-1-tosyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-2-(methylsulfonyl)pyrimidin-4-yl)piperidin-4-ylcarbamate

生成物 1

HCID 178507870HCID 178507870、化合物収率 64.2%

試薬・触媒・溶媒 2

HCID 312751,4-Dioxane
溶媒
HCID 21906603Chloroform isopropyl alcohol溶媒

反応条件

温度
100 °C

実験手順

A glass microwave reaction vessel was charged with tert-butyl 1-(6-(5-(2-fluorophenyl)-1-tosyl-1H-pyrrolo[3,2-b]pyridin-3-yl)-2-(methylsulfonyl)pyrimidin-4-yl)piperidin-4-ylcarbamate (100 mg, 0.139 mmol) and NaOH (0.3 mL, 0.600 mmol) in p-dioxane (2 mL). The reaction was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 100° C. for 1 h. The mixture was diluted with CHCl3/iPrOH (4:1) and washed with water. The organic layer was dried, filtered and concentrated. The residue was dissolved in DCM (1 mL) and TFA (200 μL, 2.60 mmol) was added. The reaction was stirred at RT for 15 min, then the solvent was removed. The residue was purified with preparative HPLC (eluting with 5-30% ACN in water in 30 min) to give 4-(4-aminopiperidin-1-yl)-6-(5-(2-fluorophenyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)pyrimidin-2-ol (36.0 mg, 0.089 mmol, 64.2% yield) as a TFA salt. MS (ESI, pos. ion) m/z: 405.0 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 12.51 (1 H, br. s.), 8.79 (1 H, d, J=3.1 Hz), 8.12 (1 H, d, J=8.6 Hz), 7.85-8.05 (4 H, m), 7.76 (1 H, dd, J=8.5, 1.9 Hz), 7.46-7.61 (2 H, m), 7.32-7.44 (2 H, m), 4.19-4.55 (2 H, m), 3.37-3.52 (2 H, m), 3.10-3.33 (2 H, m), 2.04 (2 H, d, J=11.2 Hz), 1.47-1.68 (2 H, m).

後処理

  1. customA glass microwave reaction vessel
  2. washwashed with water
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in DCM (1 mL)
  7. stirringThe reaction was stirred at RT for 15 min
  8. customthe solvent was removed
  9. customThe residue was purified with preparative HPLC (eluting with 5-30% ACN in water in 30 min)

出典と根拠

ORDレコード
ord-3ac9ff3dfe3f4170929c3b9e70c7704f
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09090593B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート