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Triethylamine → Methanone, [(3R)-1-(4-amino-5-nitro-2-pyrimidinyl)-3-piperidinyl]-1-pyrrolidinyl-

HRID 931059
ノート
印刷プレビュー

反応式

HRID 931059 の反応式
Cl[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.Cl.[NH:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]([C:19]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])[CH2:14]1.Cl.Cl.NC1C=CC(N2CCC[C@@H](C(N3CCCC3)=O)C2)=NC=1N.C(N(CC)CC)C>CS(C)=O.C(OCC)(=O)C>[NH2:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=[C:2]([N:13]2[CH2:18][CH2:17][CH2:16][C@@H:15]([C:19]([N:21]3[CH2:22][CH2:23][CH2:24][CH2:25]3)=[O:20])[CH2:14]2)[N:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 747162-Chloro-5-nitropyrimidin-4-amineHCID 89854051(R)-(1-(5,6-Diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone dihydrochlorideHCID 117966306(R)-piperidin-3-yl(pyrrolidin-1-yl)methanone hydrochloride

生成物 1

HCID 89854015Methanone, [(3R)-1-(4-amino-5-nitro-2-pyrimidinyl)-3-piperidinyl]-1-pyrrolidinyl-

試薬・触媒・溶媒

2
HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-chloro-5-nitropyrimidin-4-amine (670 mg, 3.84 mmol, 80% pure), (R)-piperidin-3-yl(pyrrolidin-1-yl)methanone hydrochloride (prepared by the method described in Steps 1 and 2 of Intermediate 1, 560 mg, 2.56 mmol) and triethylamine (0.761 mL, 5.46 mmol) in dimethylsulfoxide (5 mL) was heated to 100° C. for 5 h. The mixture was diluted with ethyl acetate (80 mL), washed with water and brine, dried over sodium sulfate and concentrated. The crude material was purified via flash chromatography (ethyl acetate/heptane: 40-70-100%) to afford (R)-(1-(4-amino-5-nitropyrimidin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone as a yellow solid (420 mg). 1H NMR (500 MHz, DMSO-d6) δ 1.45 (t, 1H), 1.62 (d, 1H), 1.72-1.82 (m, 4H), 1.88 (d, 4H), 2.56 (br s, 1H), 2.90-3.04 (m, 2H), 3.28 (t, 2H), 3.37-3.62 (m, 2H), 4.59-4.87 (m, 2H), 8.00 (br s, 1H), 8.16 (br s, 1H), 8.90 (s, 1H); MS (ES+) (M+H) 321.2.

後処理

  1. customprepared by the method
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude material was purified via flash chromatography (ethyl acetate/heptane: 40-70-100%)

出典と根拠

ORDレコード
ord-63ceb40ace2847449d9aaab732cb5115
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09296745B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート