Sodium borohydride → 6-~{tert}-Butyl-8-Fluoranyl-2-[3-(Hydroxymethyl)-4-[1-Methyl-6-Oxidanylidene-5-(Pyrimidin-4-Ylamino)pyridin-3-Yl]pyridin-2-Yl]phthalazin-1-One

HRID 407644노트

반응식

HRID 407644 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]=[CH:34][N:33]=4)[C:28](=[O:38])[N:27]([CH3:39])[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]=[CH:34][N:33]=4)[C:28](=[O:38])[N:27]([CH3:39])[CH:26]=3)[CH:22]=[CH:23][N:24]=1)[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 866839322-(6-tert-Butyl-8-fluoro-1-oxophthalazin-2(1H)-yl)-4-(1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridin-3-yl)nicotinaldehyde

생성물 1

HCID 866839336-~{tert}-Butyl-8-Fluoranyl-2-[3-(Hydroxymethyl)-4-[1-Methyl-6-Oxidanylidene-5-(Pyrimidin-4-Ylamino)pyridin-3-Yl]pyridin-2-Yl]phthalazin-1-One수율 77.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 113c (80 mg, 0.14 mmol), NaBH4 (27 mg, 0.70 mmol), and methanol (10 mL) was stirred at room temperature for 0.5 h. The mixture was quenched with water (2 mL) and concentrated under reduced pressure. The residue was purified with reverse-phase prep-HPLC to afford 113 (57 mg, 71%). MS-ESI: [M+H]+ 528.3. 1H NMR (500 MHz, DMSO-d6) δ 9.26 (s, 1H), 8.76 (d, J=2.5 Hz, 1H), 8.67 (s, 1H), 8.59 (d, J=5.0 Hz, 1H), 8.54 (d, J=2.5 Hz, 1H), 8.31 (d, J=6.0 Hz, 1H), 7.90 (d, J=1.5 Hz, 1H), 7.79-7.76 (m, 1H), 7.69 (d, J=2.0 Hz 1H), 7.54 (d, J=5.0, Hz 1H), 7.34-7.32 (m, 1H), 4.94 (t, J=5.0 Hz, 1H), 4.42-4.40 (m, 2H), 3.62 (s, 3H), 1.39 (s, 9H).

후처리

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

출처 및 근거

ORD 기록
ord-5a25a8dab3414e68a4bbcbc078c84b64
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754077B2

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