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

HRID 1436344Notes

Reaction equation

HRID 1436344 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+] calc. 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-d606903e6ca94f04a74303cac8c214f9
Source dataset
uspto-grants-2009_11
Patent number
US07618993B2

Reaction notes

Loading…