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Sodium borohydride → 6-Tert-butyl-8-fluoro-2-[3-(hydroxymethyl)-4-[1-methyl-5-[(2-methylpyrimidin-4-yl)amino]-6-oxo-3-pyridyl]-2-pyridyl]phthalazin-1-one

HRID 1185061
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HRID 1185061 반응식
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[N:24]=[CH:23][CH:22]=[C:21]([C:25]3[CH:30]=[C:29]([NH:31][C:32]4[CH:37]=[CH:36][N:35]=[C:34]([CH3:38])[N:33]=4)[C:28](=[O:39])[N:27]([CH3:40])[CH:26]=3)[C:18]=1[CH:19]=[O:20])[N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:17]1[C:18]([CH2:19][OH:20])=[C:21]([C:25]3[CH:30]=[C:29]([NH:31][C:32]4[CH:37]=[CH:36][N:35]=[C:34]([CH3:38])[N:33]=4)[C:28](=[O:39])[N:27]([CH3:40])[CH:26]=3)[CH:22]=[CH:23][N:24]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 866839342-(6-tert-Butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-(1-methyl-5-(2-methylpyrimidin-4-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)nicotinaldehyde

생성물 1

HCID 866839366-Tert-butyl-8-fluoro-2-[3-(hydroxymethyl)-4-[1-methyl-5-[(2-methylpyrimidin-4-yl)amino]-6-oxo-3-pyridyl]-2-pyridyl]phthalazin-1-one수율 15.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

At 0° C., to a suspension of 2-(6-tert-butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-(1-methyl-5-(2-methylpyrimidin-4-ylamino)-6-oxo-1,6-dihydropyridin-3-yl)nicotinaldehyde 114c (130 mg, 0.24 mmol) in methanol (20 mL) was added sodium borohydride (27 mg, 0.72 mmol). The reaction mixture was stirred for 20 minutes and then quenched with water (10 mL). It was then concentrated under reduced pressure and the residue was extracted with dichloromethane (3×20 mL). The combined organic layer was dried and concentrated under reduced pressure. The residue was purified by reverse-phase prep-HPLC to afford 114 (20 mg, 15%) as a white solid. MS-ESI: [M+H]+ 542.3. 1H NMR (500 MHz, CDCl3) 8.97 (d, J=2.5 Hz, 1H), 8.71 (d, J=5.0 Hz, 1H, 8.36 (d, J=2.0 Hz, 1H), 8.28 (d, J=5.5 Hz, 1H), 8.09-8.06 (m, 1H), 7.86 (d, J=2.5 Hz, 1H), 7.60-7.56 (m, 3H), 6.61 (d, J=6.0 Hz, 1H), 4.54-4.43 (m, 2H), 4.16-4.13 (m, 1H), 3.75 (s, 3H), 2.62 (s, 3H), 1.46 (s, 9H).

후처리

  1. customquenched with water (10 mL)
  2. concentrationIt was then concentrated under reduced pressure
  3. extractionthe residue was extracted with dichloromethane (3×20 mL)
  4. customThe combined organic layer was dried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by reverse-phase prep-HPLC

출처 및 근거

ORD 기록
ord-38e3a549ccc342ecadb8443112125f85
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08669251B2

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