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

HRID 592879ノート

反応式

HRID 592879 の反応式
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]2[N:9]=[C:10]([NH:12][C:13]3[C:18](=[O:19])[N:17]([CH3:20])[CH:16]=[C:15]([C:21]4[C:26]([CH:27]=[O:28])=[C:25]([N:29]5[CH2:41][CH2:40][C:39]6[N:38]7[C:33]([CH2:34][CH2:35][CH2:36][CH2:37]7)=[CH:32][C:31]=6[C:30]5=[O:42])[N:24]=[CH:23][CH:22]=4)[CH:14]=3)[CH:11]=[C:5]2[CH2:4]1)[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]2[N:9]=[C:10]([NH:12][C:13]3[C:18](=[O:19])[N:17]([CH3:20])[CH:16]=[C:15]([C:21]4[CH:22]=[CH:23][N:24]=[C:25]([N:29]5[CH2:41][CH2:40][C:39]6[N:38]7[C:33]([CH2:34][CH2:35][CH2:36][CH2:37]7)=[CH:32][C:31]=6[C:30]5=[O:42])[C:26]=4[CH2:27][OH:28])[CH:14]=3)[CH:11]=[C:5]2[CH2:4]1)[CH3:2]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 866843894-(5-(5-Ethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-(1-oxo-3,4,6,7,8,9-hexahydro-pyrido[3,4-b]indolizin-2(1H)-yl)nicotinaldehyde

生成物 1

HCID 715579162-[4-[5-[(5-ethyl-6,7-dihydro-4H-pyrazolo[1,5-a]pyrazin-2-yl)amino]-1-methyl-6-oxo-3-pyridyl]-3-(hydroxymethyl)-2-pyridyl]-3,4,6,7,8,9-hexahydropyrido[3,4-b]indolizin-1-one収率 9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a mixture of 208e (95 mg, 0.16 mmol) at 0° C. in methanol (10 mL) was added sodium borohydride (19 mg, 0.50 mmol). The reaction mixture was stirred for 30 minutes and quenched with water (2.0 mL). It was then concentrated under reduced pressure and the residue was purified by reverse-phase prep-HPLC to afford 208 (8 mg, 9%) as white solid. MS-ESI: [M+H]+ 569.3. 1H NMR (500 MHz, CDCl3) δ 8.46 (d, J=5.0 Hz, 1H), 7.92 (d, J=2.0 Hz, 1H, 7.70 (d, J=2.0 Hz, 1H), 7.40 (s, 1H), 7.30 (d, J=5.0 Hz, 1H), 6.30 (s, 1H), 5.71 (s, 1H), 4.93-4.96 (m, 1H), 4.63-4.61 (m, 1H), 4.42-4.26 (m, 2H), 4.09 (s, 2H), 3.94-3.81 (m, 3H), 3.69-3.68 (m, overlap, 5H), 3.06-2.90 (m, 4H), 2.81 (d, J=3.0 Hz, 2H), 2.66 (d, J=3.5 Hz, 2H), 2.04-2.00 (m, 2H), 1.88-1.85 (m, 2H), 1.20 (t, J=7.5 Hz, 3H).

後処理

  1. customquenched with water (2.0 mL)
  2. concentrationIt was then concentrated under reduced pressure
  3. customthe residue was purified by reverse-phase prep-HPLC

出典と根拠

ORDレコード
ord-a1c0412e9838485b93d8762f4e6f7ba6
出典データセット
uspto-grants-2016_01
特許番号
US09238655B2

反応ノート

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