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Formic Acid → 3-(4-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-pyrazol-1-yl)-azetidine-1-carboxylic acid dimethylamide

HRID 2046934
ノート
印刷プレビュー

反応式

HRID 2046934 の反応式
[NH:1]1[CH2:4][CH:3]([N:5]2[CH:9]=[C:8]([C:10]3[CH:11]=[C:12]4[C:18]([CH:19]([C:21]5[C:26]([Cl:27])=[CH:25][CH:24]=[C:23]([F:28])[C:22]=5[Cl:29])[CH3:20])=[CH:17][NH:16][C:13]4=[N:14][CH:15]=3)[CH:7]=[N:6]2)[CH2:2]1.C(O)=O.[CH3:33][N:34]([C:36]([O:40]N1N=NC2C=CC=CC1=2)=[N+](C)C)[CH3:35].[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:33][N:34]([CH3:35])[C:36]([N:1]1[CH2:2][CH:3]([N:5]2[CH:9]=[C:8]([C:10]3[CH:11]=[C:12]4[C:18]([CH:19]([C:21]5[C:26]([Cl:27])=[CH:25][CH:24]=[C:23]([F:28])[C:22]=5[Cl:29])[CH3:20])=[CH:17][NH:16][C:13]4=[N:14][CH:15]=3)[CH:7]=[N:6]2)[CH2:4]1)=[O:40]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 284Formic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 462154755-(1-azetidin-3-yl-1H-pyrazol-4-yl)-3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 673648073-(4-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-pyrazol-1-yl)-azetidine-1-carboxylic acid dimethylamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 5-(1-azetidin-3-yl-1H-pyrazol-4-yl)-3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine (6.0 mg, 0.014 mmol), formic acid (1.4 μL, 0.037 mmol), TBTU (8.95 mg, 0.0279 mmol), DIPEA (0.02 mL, 0.09 mmol) and DMF (1 mL) was stirred at rt for 30 min. The solution was used directly for HPLC purification. The fractions containing the material were concentrated in vacuo, redissolved in THF and treated with 5M NaOH (0.1 mL) at rt for 10 min. The solution was neutralized with HCl, and loaded into an SCX cartridge. MeOH was used to wash, and the material was ejected with 2M NH3 in MeOH to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=1.89 (d, J=7.1 Hz, 3 H), 2.92 (s, 6 H), 4.33-4.40 (m, 2 H), 4.42-4.50 (m, 2 H), 5.16-5.25 (m, 1 H), 5.25-5.35 (m, 1 H), 7.15-7.22 (m, 1 H), 7.37 (d, J=1.5 Hz, 1 H), 7.38-7.53 (m, 2 H), 7.68 (s, 1 H), 7.94 (s, 1 H), 8.33 (s, 1H). MS (ES+): m/z 501.06 (100) [MH+]. HPLC: tR=3.35 min (ZQ3, polar—5 min).

後処理

  1. customThe solution was used directly for HPLC purification
  2. additionThe fractions containing the material
  3. concentrationwere concentrated in vacuo
  4. dissolutionredissolved in THF
  5. additiontreated with 5M NaOH (0.1 mL) at rt for 10 min
  6. washto wash

出典と根拠

ORDレコード
ord-480c548da2454f6688331ba849d2e418
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08592448B2

反応ノート

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