Diisopropylethylamine → HCID 178426295, compound

HRID 251052Notes

Reaction equation

HRID 251052 reaction equation
[CH3:1][C:2]1[C:3]([CH2:8][N:9]([CH2:15][C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])=[N:4][CH:5]=[CH:6][CH:7]=1.Cl.N1C=CC([C:29]([NH2:31])=[NH:30])=N1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][C:2]1[C:3]([CH2:8][N:9]([CH2:15][C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:29]([NH2:31])=[NH:30])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11460737N1,N1-bis-(3-methyl-pyridin-2-ylmethyl)-butane-1,4-diamineHCID 178479321HCID 178479321, compound

Product 1

HCID 178426295HCID 178426295, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N1,N1-bis-(3-methyl-pyridin-2-ylmethyl)-butane-1,4-diamine (0.1970 g, 0.46 mmol) in DMF (5 mL) was added 1H-pyrazole-carboxamidine hydrochloride (0.0681 g, 0.46 mmol) and DIPEA (0.48 mL, 2.76 mmol) and stirred at room temperature for 16 hours. The reaction mixture was concentrated, and purification of the crude material by column chromatography on silica gel (20:1:1, then 10:1:1, then 1:1:1 CH2Cl2-MeOH—NH4OH) followed by radial chromatography on silica gel (20:4:1 CH2Cl2-MeOH—NH4OH) provided 0.1380 g (64%) of COMPOUND 196 as a white solid. 1H NMR (CDCl3) δ 1.49-1.53 (m, 2H), 1.65-1.69 (m, 2H), 2.17 (s, 6H), 2.70-2.75 (m, 4H), 3.12-3.14 (m, 2H), 3.87 (s, 4H), 7.10-7.14 (m, 2H), 7.41-7.44 (m, 2H), 8.34-8.39 (m, 2H). 13C NMR (CDCl3) δ 18.53, 23.14, 26.99, 41.30, 54.57, 58.09, 123.15, 133.48, 138.87, 146.21, 155.66, 158.02. ES-MS m/z 341.3 (M+H). Anal. Calcd. for C19H28N6.1.1CH2Cl2.1.8H2O: C, 51.77; H, 7.31; N, 18.02. Found: C, 51.50; H, 7.04; N, 18.31.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurification of the crude material by column chromatography on silica gel (20:1:1

Sources & evidence

ORD record
ord-eb14121774864715b7de587a358953fc
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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