Diisopropylethylamine → 1-(Cyclopropylmethyl)-2-[2-(4-ethoxyphenyl)ethyl]-N,N-diethyl-1H-benzimidazole-5-carboxamide

HRID 1796468Notes

Reaction equation

HRID 1796468 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](O)=O)=[CH:6][CH:5]=1)[CH3:2].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.[NH2:48][C:49]1[CH:50]=[C:51]([CH:59]=[CH:60][C:61]=1[NH:62][CH2:63][CH:64]1[CH2:66][CH2:65]1)[C:52]([N:54]([CH2:57][CH3:58])[CH2:55][CH3:56])=[O:53]>>[CH:64]1([CH2:63][N:62]2[C:61]3[CH:60]=[CH:59][C:51]([C:52]([N:54]([CH2:57][CH3:58])[CH2:55][CH3:56])=[O:53])=[CH:50][C:49]=3[N:48]=[C:12]2[CH2:11][CH2:10][C:7]2[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[CH:9][CH:8]=2)[CH2:65][CH2:66]1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2919853-(4-Ethoxyphenyl)propanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 221813643-amino-4-((cyclopropylmethyl)amino)-N,N-diethylbenzamide

Product 1

HCID 221813981-(Cyclopropylmethyl)-2-[2-(4-ethoxyphenyl)ethyl]-N,N-diethyl-1H-benzimidazole-5-carboxamideYield 57%

Procedure

Following general procedure 13B, 3-(4-ethoxyphenyl)propanoic acid (0.0409 g, 0.211 mmol), HATU (0.0801 g, 0.211 mmol), DIPEA (0.050 mL, 0.29 mmol), and 3-amino-4-[(cyclopropylmethyl)amino]-N,N-diethylbenzamide (0.0500 g, 0.191 mmol) were combined. The crude product was purified by column chromatography (19:1 CH2Cl2:MeOH) to provide the title compound (0.0457 g, 57%). 1H-NMR (CD3OD): δ 7.64 (s, 1H), 7.55 (d, 8.4 Hz, 1H), 7.27 (d, J=8.4 Hz, 1H), 7.08 (d, J=8.4 Hz, 2H), 6.77 (d, J=8.4 Hz, 2H), 3.97 (d, J=7.2 Hz, 2H), 3.95 (q, J=6.8 Hz, 2H), 3.57 (br s; 2H), 3.34 (br s, 2H), 3.23-3.07 (m, 4H), 1.34 (t, J=6.4 Hz, 3H), 1.36–1.02 (overlapping 2×br s and m, 7H), 0.55–0.46 (m, 2H), 0.40–0.32 (m, 2H). 13C-NMR (CD3OD): δ 174.08, 159.08, 157.72, 142.60, 136.95, 133.70, 132.03, 130.46, 121.97, 117.21, 115.59, 111.83, 64.41, 48.69, 45.15, 40.98, 34.38, 30.54, 15.18, 14.43, 13.12, 12.15, 4.54. MS (ESI) (M+H)+=420. The HCl salt was prepared using HCl in Et2O. A white solid was obtained after lyophilization. Anal. Calcd for C26H33N3O2.1.0HCl.0.8H2O: C, 66.38; H, 7.63; N, 8.93. Found: C, 66.35; H, 7.60; N, 8.81.

Workup

  1. customThe crude product was purified by column chromatography (19:1 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-106dfde0ff84496fa5433ab2a23de542
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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