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

HRID 931059
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HRID 931059 반응식
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
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참가 물질

7

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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

생성물 1

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

시약·촉매·용매

2
HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-63ceb40ace2847449d9aaab732cb5115
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09296745B2

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