Diisopropylethylamine → N-[1-(6-tert-butyl-4-methylpyridin-3-yl)ethyl]-2-(7-cyano-1H-benzimidazol-1-yl)acetamide

HRID 1919844Notes

Reaction equation

HRID 1919844 reaction equation
CC1N=CC=CC=1C(N)=O.[C:11]([C:15]1[N:20]=[CH:19][C:18]([CH:21]([NH2:23])[CH3:22])=[C:17]([CH3:24])[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>O>[C:11]([C:15]1[N:20]=[CH:19][C:18]([CH:21]([NH:23][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)[CH3:22])=[C:17]([CH3:24])[CH:16]=1)([CH3:13])([CH3:14])[CH3:12]

Participants

7

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 67501210[1-(6-Tert-butyl-4-methylpyridin-3-yl)ethyl]amine2×

Product 1

HCID 23633970N-[1-(6-tert-butyl-4-methylpyridin-3-yl)ethyl]-2-(7-cyano-1H-benzimidazol-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was synthesized according to the procedure described for the synthesis of 2-methylnicotinamide, starting from [1-(6-tert-butyl-4-methylpyridin-3-yl)ethyl]amine (intermediate 28) (52 mg, 0.27 mmol), 7-cyanobenzimidazole-1-acetic acid (54.4 mg, 0.27 mmol), HATU (108 mg, 0.28 mmol) and DIPEA (117 μL, 2.5 mmol). Water is added and the reaction is concentrated then purified by reverse phase chromatography. (Yield 31.3 mg, 31%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.27 (s, 9 H), 1.42 (d, J=7.03 Hz, 3 H), 2.29 (s, 3 H), 5.03-5.12 (m, 1 H), 5.13-5.27 (m, 2 H), 7.17 (s, 1 H), 7.34 (dd, J−8.11, 7.71 Hz, 1 H), 7.71 (dd, J=7.62, 0.78 Hz, 1 H), 8.01 (dd, J=8.01, 0.98 Hz, 1 H), 8.34 (s, 1H), 8.47 (s, 1 H), 8.88 (d, J=7.81 Hz, 1 H). MS [MH+] calc. 376.2137 found 376.3.

Workup

  1. concentrationthe reaction is concentrated
  2. customthen purified by reverse phase chromatography

Sources & evidence

ORD record
ord-829892f0bd7046b59597fbc90363d380
Source dataset
uspto-grants-2012_05
Patent number
US08168668B2

Reaction notes

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