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Sodium Sulfate → HCID 178487984, 화합물

HRID 657099
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HRID 657099 반응식
[ClH:1].[NH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][N:11]2[C:16](=[O:17])[CH:15]=[N:14][C:13]3[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[N:21][C:12]2=3)[CH2:5][CH2:4]1.[O:24]=[C:25]1[NH:36][C:29]2[N:30]=[C:31]([CH:34]=O)[N:32]=[CH:33][C:28]=2[CH2:27][CH2:26]1.C([O-])(O)=O.[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CO.[CH2:65]([Cl:67])[Cl:66]>>[CH2:65]([Cl:67])[Cl:66].[CH2:65]([Cl:67])[Cl:66].[CH3:16][OH:17].[NH4+:2].[OH-:24].[ClH:1].[CH3:23][O:22][C:20]1[CH:19]=[CH:18][C:13]2[N:14]=[CH:15][C:16](=[O:17])[N:11]([CH2:10][CH2:9][N:6]3[CH2:5][CH2:4][CH:3]([NH:2][CH2:34][C:31]4[NH:30][C:29]5=[N:36][C:25](=[O:24])[CH2:26][CH2:27][C:28]5=[CH:33][N:32]=4)[CH2:8][CH2:7]3)[C:12]=2[N:21]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 6

HCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 21226129Dichloromethane methanolHCID 594374057-Oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-2-carbaldehydeHCID 689298784-(2-(4-aminopiperidin-1-yl)ethyl)-6-methoxypyrido(2,3-b)pyrazin-3(4H)-one hydrochloride

생성물

2
HCID 86635354DCM DCM MeOH NH4OHHCID 178487984HCID 178487984, 화합물수율 43%

실험 절차

To a solution of 4-[2-(4-amino-1-piperidinyl)ethyl]-6-(methyloxy)pyrido[2,3-b]pyrazin-3(4H)-one hydrochloride (see Example 126(m) for a preparation) (0.600 g, 1.98 mmol) in 1:1 MeOH/DCM, was added 7-oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-2-carbaldehyde (0.350 g, 1.98 mmol), NaHCO3 (0.831 g, 9.90 mmol), and excess Na2SO4. The solution was stirred at ambient temperature overnight, followed by the addition of NaBH(OAc)3 (1.68 g, 7.92 mmol). The resulting solution was stirred for an additional 1 h, then concentrated onto silica gel under vacuum and the crude residue purified by column chromatography (silica gel) using a DCM/DCM-MeOH—NH4OH (90:10:1) gradient, followed by a further purification using 10% MeOH/DCM and then DCM/DCM-MeOH—NH4OH (90:1:0.1) to yield the free base of the desired product (0.396 g, 43%). LCMS: m/z 465.2 (MH+). 1H NMR (400 MHz, CDCl3) δ 1.42-1.53 (m, 2H) 1.90 (d, J=10.86 Hz, 2H) 2.18 (t, J=10.61 Hz, 2H) 2.52-2.60 (m, 1H) 2.66-2.77 (m, 5H) 2.93 (t, J=7.71 Hz, 2H) 3.07 (d, J=11.62 Hz, 2H) 3.98 (s, 2H) 4.00-4.03 (m, 3H) 4.52-4.62 (m, 2H) 6.70 (d, J=8.84 Hz, 1H) 7.99 (d, J=8.59 Hz, 1H) 8.12 (s, 1H) 8.34 (s, 1H).

후처리

  1. stirringThe resulting solution was stirred for an additional 1 h
  2. concentrationconcentrated onto silica gel under vacuum
  3. customthe crude residue purified by column chromatography (silica gel)
  4. customfollowed by a further purification

출처 및 근거

ORD 기록
ord-2e20f2547226408481964f8a09e868ed
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08071592B2

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