Chloride → Ethyl 4-{5-[(2-methylacryloyl)amino]pyridin-3-yl}-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

HRID 882122ノート

反応式

HRID 882122 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:5]=[N:6][CH:7]=1.CCN([CH:28]([CH3:30])[CH3:29])C(C)C.[Cl-].[CH3:32][OH:33]>C(Cl)Cl>[CH3:29][C:28](=[CH2:30])[C:32]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][NH:14][C:10]=3[N:11]=[CH:12][N:13]=2)[CH:5]=[N:6][CH:7]=1)=[O:33]

参加物

6

反応物 4

HCID 312ChlorideHCID 887MethanolHCID 81531DiisopropylethylamineHCID 117703138HCID 117703138、化合物

生成物 1

HCID 71599600Ethyl 4-{5-[(2-methylacryloyl)amino]pyridin-3-yl}-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To ethyl 4-(5-aminopyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (59 mg, 0.14 mmol) in DCM (1.0 mL) was added Hunig's base (0.060 mL, 0.34 mmol) at 0° C. Methacyloyl chloride (0.015 mL, 0.15 mmol) was then added dropwise and the reaction was allowed to warm to room temperature. After being stirred for 17 hours at room temperature, MeOH was added to quench the reaction and the solution was concentrated in vacuo. The crude reaction was purified by reverse phase HPLC using an acetonitrile gradient in water with 0.1% TFA modifier. The products were collected and lyophilized to afford a colorless solid. LRMS (ESI) calc'd for C18H18N5O3 [M+H]+: 352, found 352. 1H NMR (600 MHz, DMSO-D6) δ 13.17 (s, 1H), 10.22 (s, 1H), 9.04 (s, 1H), 9.02 (d, 1H, J=1.7 Hz), 8.55 (s, 1H), 8.50 (m, 1H), 8.45 (m, 1H), 5.93 (s, 1H), 5.65 (s, 1H), 3.99 (q, 2H, J=7.2 Hz), 2.01 (s, 3H), 1.00 (t, 3H, J=7.2 Hz).

後処理

  1. customto quench
  2. customthe reaction
  3. concentrationthe solution was concentrated in vacuo
  4. customThe crude reaction
  5. customwas purified by reverse phase HPLC
  6. customThe products were collected
  7. customto afford a colorless solid

出典と根拠

ORDレコード
ord-94cdc354ac3c4845a592aeae83ec1f16
出典データセット
uspto-grants-2015_03
特許番号
US08993756B2

反応ノート

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