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Sodium Sulfate → HCID 178487984、化合物

HRID 657099
ノート
印刷プレビュー

反応式

HRID 657099 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物

2
HCID 86635354DCM DCM MeOH NH4OHHCID 178487984HCID 178487984、化合物収率 43%

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2e20f2547226408481964f8a09e868ed
出典データセット
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08071592B2

反応ノート

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