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

HRID 1436347Notes

Reaction equation

HRID 1436347 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%.

Workup

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

Sources & evidence

ORD record
ord-0cd411150d6c4ff7a89f6d80ca25c8c0
Source dataset
uspto-grants-2009_11
Patent number
US07618993B2

Reaction notes

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