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 1411818노트

반응식

HRID 1411818 반응식
[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]

참가 물질

4

반응물 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

생성물 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-one수율 9%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e36d78cdc9994a53befc14de233a12ad
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921353B2

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