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Methanol → 4-Hydroxymethyl-3-[1-methyl-5-({5-[4-(oxetan-3-yl)piperazin-1-yl]pyridine-2-yl}amino)-6-oxo-1,6-dihydropyridin-3-yl]-5-{4,4-dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.02,6]dodeca-1(8), 2(6)-dien-10-yl}pyridine-4-carbaldehyde

HRID 1411483
ノート
印刷プレビュー

反応式

HRID 1411483 の反応式
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][N:19]([CH:22]4[CH2:25][O:24][CH2:23]4)[CH2:18][CH2:17]3)=[CH:12][N:11]=2)=[CH:5][C:4]([C:26]2[CH:27]=[N:28][CH:29]=[C:30]([N:34]3[CH2:45][CH2:44][C:43]4[C:42]5[CH2:41][C:40]([CH3:47])([CH3:46])[CH2:39][C:38]=5[S:37][C:36]=4[C:35]3=[O:48])[C:31]=2[CH:32]=[O:33])=[CH:3]1.[BH4-].[Na+].[CH3:51][OH:52]>>[OH:33][CH2:32][C:31]1([CH:51]=[O:52])[C:30]([N:34]2[CH2:45][CH2:44][C:43]3[C:42]4[CH2:41][C:40]([CH3:46])([CH3:47])[CH2:39][C:38]=4[S:37][C:36]=3[C:35]2=[O:48])=[CH:29][N:28]=[CH:27][CH:26]1[C:4]1[CH:5]=[C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:17][CH2:18][N:19]([CH:22]4[CH2:23][O:24][CH2:25]4)[CH2:20][CH2:21]3)=[CH:12][N:11]=2)[C:7](=[O:8])[N:2]([CH3:1])[CH:3]=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 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 866841783-[1-Methyl-5-({5-[4-(oxetan-3-yl)piperazin-1-yl]pyridine-2-yl}amino)-6-oxo-1,6-dihydropyridin-3-yl]-5-{4,4-dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.02,6]dodeca-1(8), 2(6)-dien-10-yl}pyridine-4-carbaldehyde

生成物 1

HCID 866841794-Hydroxymethyl-3-[1-methyl-5-({5-[4-(oxetan-3-yl)piperazin-1-yl]pyridine-2-yl}amino)-6-oxo-1,6-dihydropyridin-3-yl]-5-{4,4-dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.02,6]dodeca-1(8), 2(6)-dien-10-yl}pyridine-4-carbaldehyde
収率 45%

実験手順

To a solution of 106j (130 mg, 0.20 mmol) in methanol (5 mL) at 0° C. was added sodium borohydride (22 mg, 0.6 mmol) and stirred for 30 minutes. Then the reaction mixture was quenched with water (1.0 mL) and concentrated. The residue was purified by reverse-phase prep-HPLC to afford 106 (60 mg, 45%) as a yellow solid. LCMS: [M+H] 668. 1H NMR (500 MHz, DMSO) δ 8.58 (d, J=2.0, 1H), 8.56 (s, 1H), 8.49 (s, 1H), 8.41 (s, 1H), 7.87 (d, J=2.5, 1H), 7.38-7.36 (m, 2H), 7.24-7.22 (m, 1H), 5.15 (t, J=5.0, 1H), 4.56-4.42 (m, 6H), 4.08-4.04 (m, 2H), 3.60 (s, 3H), 3.43-3.42 (m, 1H), 3.07-2.94 (m, 6H), 2.55-2.53 (m, 4H), 2.39-2.38 (m, 4H), 1.23 (s, 6H)

後処理

  1. customThen the reaction mixture was quenched with water (1.0 mL)
  2. concentrationconcentrated
  3. customThe residue was purified by reverse-phase prep-HPLC

出典と根拠

ORDレコード
ord-1168a5f91d714560bf92860867eff8b3
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08921353B2

反応ノート

読み込み中…

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