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

HRID 1919845Notes

Reaction equation

HRID 1919845 reaction equation
CC1N=CC=CC=1C(N)=O.[C:11]([C:15]1[N:20]=[C:19]([Cl:21])[C:18]([CH:22]([NH2:24])[CH3:23])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].[C:25]([C:27]1[C:32]2[N:33]([CH2:36][C:37](O)=[O:38])[CH:34]=[N:35][C:31]=2[CH:30]=[CH:29][CH:28]=1)#[N:26].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]([Cl:21])[C:18]([CH:22]([NH:24][C:37](=[O:38])[CH2:36][N:33]2[C:32]3[C:27]([C:25]#[N:26])=[CH:28][CH:29]=[CH:30][C:31]=3[N:35]=[CH:34]2)[CH3:23])=[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 86621593[1-(6-Tert-butyl-2-chloropyridin-3-yl)ethyl]amine2×

Product 1

HCID 23633971N-[1-(6-tert-butyl-2-chloropyridin-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-chloropyridin-3-yl)ethyl]amine (intermediate 26) (100 mg, 0.47 mmol), 7-cyanobenzimidazole-1-acetic acid (0.42 mmol), HATU (191 mg, 0.5 mmol) and DIPEA (182 μL, 1.41 mmol). The product was recovered by filtration following precipitation induced by the addition of water. Yield 111 mg, 67%. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.27 (s, 9 H), 1.38 (d, J=7.03 Hz, 3 H), 5.05-5.13 (m, 1 H), 5.21-5.32 (m, 2 H), 7.34 (dd, J=8.01, 7.62 Hz, 1 H), 7.43 (d, J=8.01 Hz, 1 H), 7.71 (dd, J=7.62, 0.98 Hz, 1 H), 7.86 (d, J=8.01 Hz, 1 H), 8.01 (dd, J=8.01, 0.98 Hz, 1 H), 8.34 (s, 1 H), 9.06 (d, J=7.23 Hz, 1 H). MS [MH+] calc. 396.1591 found 396.3.

Workup

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

Sources & evidence

ORD record
ord-9e683639db5348d8adf959e089dae2ad
Source dataset
uspto-grants-2012_05
Patent number
US08168668B2

Reaction notes

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