3-Aminopyridine → HCID 44235022, 화합물

HRID 1093843노트

반응식

HRID 1093843 반응식
CCN(C(C)C)C(C)C.[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[CH:20]=[C:19]([C:21]([NH:23][CH2:24][C:25]([OH:27])=O)=[O:22])[N:18]=[N:17]2)[CH:11]=1.NC1C=NC=CC=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH3:57][C:58]1[CH:65]=[CH:64][C:61]([C:62]#[N:63])=[CH:60][C:59]=1[O:66][CH:67]1[CH2:72][CH2:71][NH:70][CH2:69][CH2:68]1>CN(C=O)C.O>[C:62]([C:61]1[CH:64]=[CH:65][C:58]([CH3:57])=[C:59]([CH:60]=1)[O:66][CH:67]1[CH2:68][CH2:69][N:70]([C:25](=[O:27])[CH2:24][NH:23][C:21]([C:19]2[N:18]=[N:17][N:16]([C:12]3[CH:11]=[N:10][CH:15]=[CH:14][CH:13]=3)[CH:20]=2)=[O:22])[CH2:71][CH2:72]1)#[N:63]

참가 물질

9

반응물 6

HCID 100093-AminopyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66591676HCID 66591676, 화합물HCID 66592012[(1-pyridin-3-yl-1H-[1,2,3]triazole-4-carbonyl)-amino]-acetic acid

생성물 1

HCID 44235022HCID 44235022, 화합물수율 49.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

DIPEA (94.1 mg, 0.72 mmol) was added to a stirred solution of [(1-pyridin-3-yl-1H-[1,2,3]triazole-4-carbonyl)-amino]-acetic acid (45 mg, 0.18 mmol) (prepared by the method used for the synthesis of Intermediate 64, starting from 3-aminopyridine, and subsequently, application of Step 3 of the General Scheme) in DMF (2 mL) followed by HOBt (27 mg, 0.2 mmol) and EDCI (69.8 mg, 0.366 mmol). After 2 minutes of stirring, 4-methyl-3-(piperidin-4-yloxy)-benzonitrile hydrochloride (prepared by the method used for the synthesis of Intermediate 15) (50.6 mg, 0.2 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was added and the precipitate was collected. The solid was purified by stirring in mixture of DCM in hexane to afford 40 mg (49.2% Yield) of 1-pyridin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid {2-[4-(5-cyano-2-methyl-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 446.19, 96.84%. 1H NMR (300 MHz, DMSO-d6): δ 9.45 (s, 1H), 9.2 (d, 1H), 8.75 (d, 1H), 8.55-8.45 (t, 1H), 8.4 (m, 1H), 7.72-7.64 (m, 1H), 7.55 (s, 1H), 7.4-7.3 (q, 2H), 4.8 (m, 1H), 4.25 (d, 2H), 3.8-3.6 (m, 2H), 3.5-3.4 (m, 2H), 2.25 (s, 3H), 2.1-1.8 (m, 2H), 1.8-1.5 (m, 2H).

후처리

  1. customprepared by the method
  2. additionwas added
  3. stirringthe resulting mixture was stirred at room temperature overnight
  4. customthe precipitate was collected
  5. customThe solid was purified
  6. stirringby stirring in mixture of DCM in hexane

출처 및 근거

ORD 기록
ord-5ad5fdd0f8d14b9fa288a9485d4a730f
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129376B2

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