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Diisopropylethylamine → N-[1-(6-tert-butylpyridin-3-yl)ethyl]-2-(7-cyano-1H-benzimidazol-1-yl)acetamide

HRID 1919846
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HRID 1919846 반응식
CC1N=CC=CC=1C(N)=O.[C:11]([C:15]1[N:20]=[CH:19][C:18]([CH:21]([NH2:23])[CH3:22])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].[C:24]([C:26]1[C:31]2[N:32]([CH2:35][C:36](O)=[O:37])[CH:33]=[N:34][C:30]=2[CH:29]=[CH:28][CH:27]=1)#[N:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>O>[C:11]([C:15]1[N:20]=[CH:19][C:18]([CH:21]([NH:23][C:36](=[O:37])[CH2:35][N:32]2[C:31]3[C:26]([C:24]#[N:25])=[CH:27][CH:28]=[CH:29][C:30]=3[N:34]=[CH:33]2)[CH3:22])=[CH:17][CH:16]=1)([CH3:14])([CH3:12])[CH3:13]
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참가 물질

7

반응물 5

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11195002(7-Cyano-1H-benzimidazol-1-yl)acetic acidHCID 122437052-MethylnicotinamideHCID 67500288[1-(6-Tert-butylpyridin-3-yl)ethyl]amine2회

생성물 1

HCID 23633972
N-[1-(6-tert-butylpyridin-3-yl)ethyl]-2-(7-cyano-1H-benzimidazol-1-yl)acetamide

시약·촉매·용매 1

HCID 962Water용매

실험 절차

The title compound was synthesized according to the procedure described for the synthesis of 2-methylnicotinamide, starting from [1-(6-tert-butylpyridin-3-yl)ethyl]amine (intermediate 25) (93 mg, 0.52 mmol), 7-cyanobenzimidazole-1-acetic acid (100 mg, 0.5 mmol), HATU (198 mg, 0.52 mmol) and DIPEA (226 μL, 1.3 mmol). Water is added and the reaction is concentrated then purified by reverse phase chromatography. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.26 (s, 9 H), 1.39 (d, J=7.03 Hz, 3 H), 4.87-4.97 (m, 1 H), 5.12-5.27 (m, 2 H), 7.32 (dd, J=8.01, 7.62 Hz, 1 H), 7.35 (d, J=8.20 Hz, 1 H), 7.66 (dd, J=8.30, 2.25 Hz, 1 H), 7.69 (dd, J=7.52, 0.88 Hz, 1 H), 7.99 (dd, J=8.20, 0.98 Hz, 1 H), 8.32 (s, 1H), 8.45 (d, J=2.54 Hz, 1 H), 8.85 (d, J=7.42 Hz, 1 H). MS [MH+] calc. 362.1981 found 362.3.

후처리

  1. concentrationthe reaction is concentrated
  2. customthen purified by reverse phase chromatography

출처 및 근거

ORD 기록
ord-a0e4d1c240ed480394fce2256d60ce69
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08168668B2

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