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

HRID 1919846Notes

Reaction equation

HRID 1919846 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])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].[C:24]([C:26]1[C:31]2[N:32]([CH2:35][C:36](O)=[O:37])[CH:33]=[N:34][C:30]=2[CH:29]=[CH:28][CH:27]=1)#[N:25].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:36](=[O:37])[CH2:35][N:32]2[C:31]3[C:26]([C:24]#[N:25])=[CH:27][CH:28]=[CH:29][C:30]=3[N:34]=[CH:33]2)[CH3:22])=[CH:17][CH:16]=1)([CH3:14])([CH3:12])[CH3:13]

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 67500288[1-(6-Tert-butylpyridin-3-yl)ethyl]amine2×

Product 1

HCID 23633972N-[1-(6-tert-butylpyridin-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-butylpyridin-3-yl)ethyl]amine (intermediate 25) (93 mg, 0.52 mmol), 7-cyanobenzimidazole-1-acetic acid (100 mg, 0.5 mmol), HATU (198 mg, 0.52 mmol) and DIPEA (226 μL, 1.3 mmol). Water is added and the reaction is concentrated then purified by reverse phase chromatography. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.26 (s, 9 H), 1.39 (d, J=7.03 Hz, 3 H), 4.87-4.97 (m, 1 H), 5.12-5.27 (m, 2 H), 7.32 (dd, J=8.01, 7.62 Hz, 1 H), 7.35 (d, J=8.20 Hz, 1 H), 7.66 (dd, J=8.30, 2.25 Hz, 1 H), 7.69 (dd, J=7.52, 0.88 Hz, 1 H), 7.99 (dd, J=8.20, 0.98 Hz, 1 H), 8.32 (s, 1H), 8.45 (d, J=2.54 Hz, 1 H), 8.85 (d, J=7.42 Hz, 1 H). MS [MH+] calc. 362.1981 found 362.3.

Workup

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

Sources & evidence

ORD record
ord-a0e4d1c240ed480394fce2256d60ce69
Source dataset
uspto-grants-2012_05
Patent number
US08168668B2

Reaction notes

Loading…