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Sodium borohydride → 2-[3-(hydroxymethyl)-4-[1-methyl-5-[(5-methyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazin-2-yl)amino]-6-oxo-3-pyridyl]-2-pyridyl]-6,7,8,9-tetrahydropyrazino[1,2-a]indol-1-one

HRID 592827
ノート
印刷プレビュー

反応式

HRID 592827 の反応式
[CH:1]([C:3]1[C:4]([N:28]2[CH:40]=[CH:39][N:31]3[C:32]4[CH2:33][CH2:34][CH2:35][CH2:36][C:37]=4[CH:38]=[C:30]3[C:29]2=[O:41])=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:25]=[C:19]3[CH2:20][N:21]([CH3:24])[CH2:22][CH2:23][N:18]3[N:17]=2)[C:12](=[O:26])[N:11]([CH3:27])[CH:10]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[C:4]([N:28]2[CH:40]=[CH:39][N:31]3[C:32]4[CH2:33][CH2:34][CH2:35][CH2:36][C:37]=4[CH:38]=[C:30]3[C:29]2=[O:41])=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[C:13]([NH:15][C:16]2[CH:25]=[C:19]3[CH2:20][N:21]([CH3:24])[CH2:22][CH2:23][N:18]3[N:17]=2)[C:12](=[O:26])[N:11]([CH3:27])[CH:10]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 866843592-(3-(Formyl)-4-(1-methyl-5-(5-methyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)pyridin-2-yl)-6,7,8,9-tetrahydro-pyrazino[1,2-a]indol-1(2H)-one

生成物 1

HCID 895396192-[3-(hydroxymethyl)-4-[1-methyl-5-[(5-methyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazin-2-yl)amino]-6-oxo-3-pyridyl]-2-pyridyl]-6,7,8,9-tetrahydropyrazino[1,2-a]indol-1-one収率 58%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

実験手順

To a solution of 195g (120 mg, 0.22 mmol) in methanol (5 mL) at 0° C. was added sodium borohydride (25 mg, 0.66 mmol). The reaction mixture was stirred for 30 minutes. It was then quenched with water (1.0 mL) and concentrated under reduced pressure. The residue was purified by reverse-phase prep-HPLC to afford 195 (70 mg, 58%). MS-ESI: [M+H]+ 553.3. 1H NMR (500 MHz, CDCl3) δ 8.56 (d, J=5.0 Hz, 1H), 7.99 (d, J=2.0 Hz, 1H), 7.75 (d, J=2.0 Hz, 1H), 7.49 (d, J=4.5 Hz, 1H), 7.43 (s, 1H), 7.07 (s, 1H), 6.97 (d, J=6.0 Hz, 1H), 6.67 (d, J=6.0 Hz, 1H), 5.70 (s, 1H), 5.08-5.06 (m, 1H), 4.51-4.49 (m, 1H), 4.36-4.34 (m, 1H), 4.14-4.05 (m, 2H), 3.72 (s, 3H), 3.62-3.60 (m, 2H), 2.91-2.89 (m, 2H), 2.75-2.70 (m, 4H), 2.49 (s, 3H), 1.97-1.95 (m, 2H), 1.86-1.84 (m, 2H).

後処理

  1. customIt was then quenched with water (1.0 mL)
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by reverse-phase prep-HPLC

出典と根拠

ORDレコード
ord-bd5fb54fad3f487da86f2ed2a6eb5b37
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09238655B2

反応ノート

読み込み中…

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