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1-Hydroxybenzotriazole → 5-Phenylamino-pyridine-2-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide

HRID 1093663
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HRID 1093663 반응식
[C:1]1([NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]([NH:16][CH2:17][C:18]([OH:20])=O)=[O:15])=[N:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.Cl.[NH:54]1[CH2:59][CH2:58][CH:57]([NH:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][C:62]=2[Cl:67])[CH2:56][CH2:55]1>CN(C=O)C.O>[Cl:67][C:62]1[CH:63]=[CH:64][CH:65]=[CH:66][C:61]=1[NH:60][CH:57]1[CH2:58][CH2:59][N:54]([C:18](=[O:20])[CH2:17][NH:16][C:14]([C:11]2[CH:10]=[CH:9][C:8]([NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:13][N:12]=2)=[O:15])[CH2:55][CH2:56]1
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참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57874471[(5-Phenylamino-pyridine-2-carbonyl)-amino]-acetic acidHCID 66591362(2-Chloro-phenyl)-piperidin-4-yl-amine dihydrochloride

생성물 1

HCID 44233265
5-Phenylamino-pyridine-2-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide
수율 64%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of [(5-phenylamino-pyridine-2-carbonyl)-amino]-acetic acid (0.035 g, 0.00013 mol) in DMF (1 mL) was added DIPEA (0.05 g, 0.00039 mol), HOBt (0.0209 g, 0.00015 mol) and EDCI.HCl (0.0296 g, 0.00015 mol) at ambient temperature. After 2 minutes piperidin-4-yl-(2-chloro-phenyl)-amine dihydrochloride (0.0382 g, 0.00015 mol) was added and the resulting mixture was stirred overnight. The reaction mixture was then diluted with cold water and the resulting precipitate was isolated by filtration and dried to afford 0.038 g (64%) of 5-phenylamino-pyridine-2-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LCMS: 464.18 (M+1)+, 92.88%, 1H NMR (DMSO-d6): δ 8.9 (s, 1H), 8.5 (t, 1H), 8.3 (d, 1H), 7.9 (d, 1H), 7.55 (dd, 1H), 7.35 (t, 2H), 7.2 (m, 4H), 7.0 (t, 1H), 6.9 (d, 1H), 6.6 (t, 1H), 4.9 (d, 1H), 4.35 (d, 1H), 4.2 (d, 2H), 3.85 (d, 1H), 3.55 (s, 1H), 3.2 (m, 2H), 2.85 (m, 1H), 1.95 (t, 2H), 1.5 (m, 1H), 1.35 (m, 1H).

후처리

  1. customthe resulting precipitate was isolated by filtration
  2. customdried

출처 및 근거

ORD 기록
ord-12cf79792d6a4df4872086b0033a4e32
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08129376B2

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