Trifluoroacetic acid → (3S)-3-amino-1-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperidin-2-one

HRID 57934ノート

反応式

HRID 57934 の反応式
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[N:13]=[CH:12][C:11]3[CH:14]=[N:15][N:16]([C:17]4[N:22]=[C:21]([N:23]5[CH2:28][CH2:27][CH2:26][C@H:25]([NH:29]C(=O)OC(C)(C)C)[C:24]5=[O:37])[CH:20]=[CH:19][CH:18]=4)[C:10]=3[CH:9]=2)[CH:5]=[N:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:29][C@H:25]1[CH2:26][CH2:27][CH2:28][N:23]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([N:16]3[C:10]4[CH:9]=[C:8]([C:6]5[CH:5]=[N:4][CH:3]=[C:2]([CH3:1])[N:7]=5)[N:13]=[CH:12][C:11]=4[CH:14]=[N:15]3)[N:22]=2)[C:24]1=[O:37]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86707119tert-butyl N-[(3S)-1-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-2-oxo-3-piperidyl]carbamate

生成物 1

HCID 72714481(3S)-3-amino-1-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperidin-2-one収率 39.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of tert-butyl N-[(3S)-1-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-2-oxo-3-piperidyl]carbamate (140 mg, 0.280 mmol) in dichloromethane 4.0 ml and trifluoroacetic acid (0.80 ml, 10 mmol) was stirred at RT 3 h. The reaction was concentrated and diluted with water then extracted with EtOAc. The aqueous layer was basified with 1M NaOH to pH 10 then extracted with EtOAc. The organic layers was dried with sodium sulfate, filtered, and concentrated in vacuum. The crude product was submitted for reverse phase HPLC to give 225 (44 mg, 39% yield). MS (ESI) m/z: 401.1. 1H NMR (400 MHz, DMSO) δ 9.60 (s, 1H), 9.47 (s, 1H), 9.33 (s, 1H), 8.72 (s, 1H), 8.64 (s, 1H), 8.05 (t, J=8.1 Hz, 1H), 7.82 (d, J=8.0 Hz, 1H), 7.74 (d, J=8.1 Hz, 1H), 4.46-4.33 (m, 1H), 4.14-4.02 (m, 1H), 3.58 (dd, J=10.8, 6.4 Hz, 1H), 2.65 (s, 3H), 2.24 (dt, J=11.4, 5.3 Hz, 1H), 2.19-2.00 (m, 2H), 1.77 (ddd, J=23.0, 10.6, 5.1 Hz, 1H).

後処理

  1. concentrationThe reaction was concentrated
  2. additiondiluted with water
  3. extractionthen extracted with EtOAc
  4. extractionthen extracted with EtOAc
  5. dry with materialThe organic layers was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum

出典と根拠

ORDレコード
ord-faccf07d6c8a40169f83e72ba6a327c5
出典データセット
uspto-grants-2016_09
特許番号
US09434725B2

反応ノート

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