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

HRID 1919842Notes

Reaction equation

HRID 1919842 reaction equation
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]

Participants

6

Reactant 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]amine2×

Product 1

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

Procedure

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+] cal. 392.2086 found 392.3.

Workup

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

Sources & evidence

ORD record
ord-cb6f074a06d34ed48b31e22c6a51e81b
Source dataset
uspto-grants-2012_05
Patent number
US08168668B2

Reaction notes

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