1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58997200, compound

HRID 251165Notes

Reaction equation

HRID 251165 reaction equation
[CH3:1][C:2]1[C:3]([CH2:9][N:10]([CH2:17][C:18]2[C:23]([CH:24]([CH3:26])[CH3:25])=[CH:22][CH:21]=[CH:20][N:19]=2)[CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[NH:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[C:36](O)=[O:37].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl.C([O-])(O)=O.[Na+]>[NH:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[C:36]([N:14]1[CH2:15][CH2:16][CH:11]([N:10]([CH2:9][C:3]2[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][N:4]=2)[CH2:17][C:18]2[C:23]([CH:24]([CH3:26])[CH3:25])=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:12][CH2:13]1)=[O:37]

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2332402-Benzimidazolecarboxylic acidHCID 58997074(3,5-Dimethyl-pyridin-2-ylmethyl)-(3-isopropyl-pyridin-2-ylmethyl)-piperidin-4-yl-amine

Product 1

HCID 58997200HCID 58997200, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of the (3,5-dimethyl-pyridin-2-ylmethyl)-(3-isopropyl-pyridin-2-ylmethyl)-piperidin-4-yl-amine (211 mg, 0.60 mmol), 1H-benzimidazole-2-carboxylic acid (107 mg, 0.66 mmol), HOBT (97 mg, 0.72 mmol), EDCI (142 mg, 0.72 mmol), and DIPEA (142 mg, 0.72 mmol) in DMF (5 mL) was stirred at room temperature overnight. The mixture was then diluted with CH2Cl2 (25 mL) and saturated NaHCO3 (3×20 mL). The organic layer was dried (MgSO4), filtered, and concentrated to afford a yellow oil. Purification by radial chromatography on silica gel (2 mm plate; using CH2Cl2/MeOH/NH4OH; 100:1:1→25:1:1) afforded the product as a white foam (160 mg, 54%). 1H NMR (CDCl3) δ 0.93 (t, 2H, J=6.9 Hz), 1.69-1.92 (m, 2H), 2.09 (br t, 3H, J=14.7 Hz), 2.18 (s, 3H), 2.27 (s, 3H), 2.68-2.83 (m, 2H), 2.87-2.94 (m, 1H), 3.04-3.13 (m, 1H), 3.79 (d, 2H, J=5.1 Hz), 3.86 (s, 2H), 4.94 (d, 1H, J=13.5 Hz), 6.16 (d, 1H, J=12.9 Hz), 7.15 (dd, 1H, J=7.8, 4.8 Hz), 7.25 (s, 1H), 7.31 (d, 2H, J=3.9 Hz), 7.50 (d, 2H, J=6.6 Hz), 7.82 (br s, 1H), 8.19 (s, 1H), 8.34 (dd, 1H, J=4.7, 1.2 Hz). 13C NMR (CDCl3) δ 18.31, 18.53, 23.60, 23.68, 27.35, 27.42, 28.66, 44.20, 47.20, 54.34, 57.35, 112.35, 121.26, 123.22, 125.11, 132.31, 133.26, 133.61, 133.92, 139.10, 143.52, 144.45, 145.85, 146.09, 146.64, 154.45, 156.28, 159.23. ES-MS m/z 497 [M+H]+. Anal. Calcd. for C30H36N6O.—0.8CH2Cl2: C, 65.52; H, 6.71; N, 14.88. Found: C, 65.54; H, 6.62; N, 15.11.

Workup

  1. dry with materialThe organic layer was dried (MgSO4)
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customto afford a yellow oil
  5. customPurification by radial chromatography on silica gel (2 mm plate; using CH2Cl2/MeOH/NH4OH; 100:1:1→25:1:1)

Sources & evidence

ORD record
ord-f393e21b1ed245539834c511b93717b1
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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