Diisopropylethylamine → HCID 178430553, compound

HRID 1592482Notes

Reaction equation

HRID 1592482 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:16][C:17]1[C:22]([C:23]([OH:26])([CH3:25])[CH3:24])=[CH:21][CH:20]=[CH:19][N:18]=1)[CH2:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[CH:10][N:9]=1.Cl.N1C=CC([C:33]([NH2:35])=[NH:34])=N1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:14][C:13]1[C:8]([CH2:7][N:6]([CH2:16][C:17]2[C:22]([C:23]([OH:26])([CH3:24])[CH3:25])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:33]([NH2:35])=[NH:34])=[N:9][CH:10]=[C:11]([CH3:15])[CH:12]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 589969892-(2-{[(4-Amino-butyl)-(3,5-dimethyl-pyridin-2-ylmethyl)-amino]-methyl}-pyridin-3-yl)-propan-2-olHCID 178479321HCID 178479321, compound

Product 1

HCID 178430553HCID 178430553, compoundYield 122.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-{[(4-Amino-butyl)-(3,5-dimethyl-pyridin-2-ylmethyl)-amino]-methyl}-pyridin-3-yl)-propan-2-ol (0.1423 g, 0.28 mmol) in DMF (3 mL) was adde 1H-pyrazole-carboxamidine hydrochloride (0.0440 g, 0.28 mmol) and DIPEA (0.29 mL, 1.68 mmol) and stirred at room temperature for 20 hours. The reaction mixture was concentrated, and purification of the crude material by column chromatography on silica gel (5:1:1 CH2Cl2-MeOH—NH4OH) followed by radial chromatography on silica gel (10:2:1 CH2Cl2-MeOH—NH4OH) provided 0.1367 g (41%) of COMPOUND 197 as a white solid. 1H NMR (CDCl3) δ 1.43-1.48 (m, 8H), 1.68-1.70 (m, 2H), 2.21 (s, 3H), 2.25 (s, 3H), 2.71-2.73 (m, 4H), 3.15-3.17 (m, 3H), 3.47 (s, 2H), 3.91 (s, 2H), 4.32 (s, 2H), 7.18-7.21 (m, 1H), 7.59-7.63 (m, 1H), 7.92-7.93 (m, 1H), 8.17 (s, 1H), 8.37-8.39 (m, 1H). 13C NMR (CDCl3) δ 18.31, 18.65, 22.77, 26.67, 31.59, 41.57, 54.09, 56.32, 61.95, 72.43, 123.57, 132.52, 132.92, 135.02, 139.67, 144.31, 146.94, 147.10, 150.68, 153.40, 158.00. ES-MS m/z 400 (M+H). Anal. Calcd. for C22H34N6O.1.9CH2Cl2O.1.5H2O: C, 48.91; H, 7.01; N, 14.32. Found: C, 48.68; H, 6.83; N, 14.68.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurification of the crude material by column chromatography on silica gel (5:1:1 CH2Cl2-MeOH—NH4OH)

Sources & evidence

ORD record
ord-d78774f3e81f4fa29b03acfec3ecb3e4
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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