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

HRID 1436344
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HRID 1436344 반응식
CC1N=CC=CC=1C(N)=O.[C:11]([C:15]1[N:20]=[C:19]([O:21][CH3:22])[C:18]([CH:23]([NH2:25])[CH3:24])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].[C:26]([C:28]1[C:33]2[N:34]([CH2:37][C:38](O)=[O:39])[CH:35]=[N:36][C:32]=2[CH:31]=[CH:30][CH:29]=1)#[N:27].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>>[C:11]([C:15]1[N:20]=[C:19]([O:21][CH3:22])[C:18]([CH:23]([NH:25][C:38](=[O:39])[CH2:37][N:34]2[C:33]3[C:28]([C:26]#[N:27])=[CH:29][CH:30]=[CH:31][C:32]=3[N:36]=[CH:35]2)[CH3:24])=[CH:17][CH:16]=1)([CH3:14])([CH3:12])[CH3:13]
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참가 물질

6

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 67499814[1-(6-Tert-butyl-2-methoxypyridin-3-yl)ethyl]amine2회

생성물 1

HCID 23633968
N-[1-(6-tert-butyl-2-methoxypyridin-3-yl)ethyl]-2-(7-cyano-1H-benzimidazol-1-yl)acetamide

실험 절차

The title compound was synthesized according to the procedure described for the synthesis of 2-methylnicotinamide, starting from [1-(6-tert-butyl-2-methoxypyridin-3-yl)ethyl]amine (intermediate 27) (85 mg, 0.48 mmol), 7-cyanobenzimidazole-1-acetic acid (96 mg 0.48 mmol) HATU (173 mg, 0.5 mmol) and DIPEA (209 μl, 1.20 mmol). The product was recovered by filtration following precipitation induced by the addition of water. (Yield 27 mg, 46%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.27 (s, 9 H), 1.32 (d, J=6.84 Hz, 3 H), 3.86 (s, 3 H), 5.02 (t, J=7.03 Hz, 1 H), 5.25 (d, J=4.69 Hz, 2 H), 6.91 (d, J=7.62 Hz, 1 H), 7.31-7.37 (m, 1 H), 7.62 (dd, J=7.62, 0.39 Hz, 1 H), 7.71 (dd, J=7.71, 1.07 Hz, 1 H), 8.01 (dd, J=8.20, 0.98 Hz, 1 H), 8.34 (s, 1 H), 8.78-8.83 (m, J=7.81 Hz, 1 H). MS [MH+] calc. 392.2086 found 392.3.

후처리

  1. filtrationThe product was recovered by filtration
  2. customprecipitation
  3. additioninduced by the addition of water

출처 및 근거

ORD 기록
ord-d606903e6ca94f04a74303cac8c214f9
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07618993B2

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