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Diisopropylethylamine → 4-Amino-N-((1-((2-(pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methyl)picolinamide

HRID 2407812
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HRID 2407812 반응식
Cl.Cl.Cl.[N:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[S:11][C:12]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][NH2:23])[CH2:18][CH2:17]2)=[CH:13][N:14]=1.Cl.C(N=C=NCCCN(C)C)C.[NH2:36][C:37]1[CH:42]=[CH:41][N:40]=[C:39]([C:43](O)=[O:44])[CH:38]=1.O.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C>CC(N(C)C)=O.C(OCC)(=O)C>[NH2:36][C:37]1[CH:42]=[CH:41][N:40]=[C:39]([C:43]([NH:23][CH2:22][CH:19]2[CH2:18][CH2:17][N:16]([CH2:15][C:12]3[S:11][C:10]([C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][N:4]=4)=[N:14][CH:13]=3)[CH2:21][CH2:20]2)=[O:44])[CH:38]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 20501324-Aminopicolinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 66989375(1-((2-(Pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methanamine Trihydrochloride

생성물 1

HCID 58504169
4-Amino-N-((1-((2-(pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methyl)picolinamide
수율 11.1%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

실험 절차

The compound prepared in Example 214 (0.44 g), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (0.25 g), 4-aminopicolinic acid (0.18 g), 1-hyroxybenzotriazole hydrate (0.20 g) and N-ethyl-N-isopropylpropan-2-amine (1.2 ml) were combined in dimethylacetamide (8 mL) and the reaction was allowed to stir 2 days. The reaction was diluted with ethyl acetate and washed with aqueous sodium bicarbonate and brine. The organic phase was dried over magnesium sulfate, filtered, concentrated and purified by column chromatography using an eluant (2 to 6% methanol/dichloromethane) to provide the title compound (0.05 g) with the following physical data.

후처리

  1. washwashed with aqueous sodium bicarbonate and brine
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-1d14aff530ac48a283d8972f76fe3314
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08809538B2

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