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Formaldehyde → 3-cyclopropyl-3-(4-(7-(7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-3-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile

HRID 1853008
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반응식

HRID 1853008 반응식
[CH:1]1([CH:4]([N:8]2[CH:12]=[C:11]([C:13]3[N:18]4[CH:19]=[CH:20][N:21]=[C:17]4[CH:16]=[C:15]([C:22]4[N:26]5[CH2:27][CH2:28][NH:29][CH2:30][C:25]5=[N:24][CH:23]=4)[N:14]=3)[CH:10]=[N:9]2)[CH2:5][C:6]#[N:7])[CH2:3][CH2:2]1.C=O.[C:33](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CO>[CH:1]1([CH:4]([N:8]2[CH:12]=[C:11]([C:13]3[N:18]4[CH:19]=[CH:20][N:21]=[C:17]4[CH:16]=[C:15]([C:22]4[N:26]5[CH2:27][CH2:28][N:29]([CH3:33])[CH2:30][C:25]5=[N:24][CH:23]=4)[N:14]=3)[CH:10]=[N:9]2)[CH2:5][C:6]#[N:7])[CH2:3][CH2:2]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 674584083-Cyclopropyl-3-(4-(7-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-3-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile

생성물 1

HCID 534974793-cyclopropyl-3-(4-(7-(7-methyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-3-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile수율 48.4%

시약·촉매·용매 1

HCID 21226129
Dichloromethane methanol
용매

실험 절차

To 3-cyclopropyl-3-(4-(7-(5,6,7,8-tetrahydroimidazo[1,2-a]pyrazin-3-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile (Example 56; 10 mg, 0.025 mmol) in DCM/MeOH (1 mL/1 mL) was added formaldehyde (50 mg, 0.50 mmol) and sodium triacetoxyborohydride (16 mg, 0.075 mmol). The reaction mixture was stirred at ambient temperature for 30 minutes and concentrated under reduced pressure. The residue was purified by silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1) to give the final product (5.0 mg, 48% yield). MS (apci) m/z=414.4 (M+H).

후처리

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel chromatography (DCM/MeOH/NH4OH 10:1:0.1)

출처 및 근거

ORD 기록
ord-5995ed2b322b40d7b80779820c786658
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08962596B2

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