Sodium triacetoxyborohydride → 1-{4-[(3,5-Dimethyl-pyridin-2-ylmethyl)-(3-isopropyl-pyridin-2-ylmethyl)-amino]-butyl}-3-hydroxy-imidazolidin-2-one

HRID 251008Notes

Reaction equation

HRID 251008 reaction equation
[CH3:1][C:2]1[C:3]([CH2:9][NH:10][CH2:11][C:12]2[C:17]([CH:18]([CH3:20])[CH3:19])=[CH:16][CH:15]=[CH:14][N:13]=2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[OH:21][N:22]1[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][CH2:29][CH:30]=O)[C:23]1=[O:32].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:1][C:2]1[C:3]([CH2:9][N:10]([CH2:11][C:12]2[C:17]([CH:18]([CH3:20])[CH3:19])=[CH:16][CH:15]=[CH:14][N:13]=2)[CH2:30][CH2:29][CH2:28][CH2:27][N:24]2[CH2:25][CH2:26][N:22]([OH:21])[C:23]2=[O:32])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 67273351(3,5-Dimethyl-pyridin-2-ylmethyl)-(3-isopropyl-pyridin-2-ylmethyl)-amineHCID 865947624-(3-Hydroxy-2-oxo-imidazolidin-1-yl)-butyraldehyde

Product 1

HCID 589972461-{4-[(3,5-Dimethyl-pyridin-2-ylmethyl)-(3-isopropyl-pyridin-2-ylmethyl)-amino]-butyl}-3-hydroxy-imidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B: Reaction of (3,5-Dimethyl-pyridin-2-ylmethyl)-(3-isopropyl-pyridin-2-ylmethyl)-amine and 4-(3-Hydroxy-2-oxo-imidazolidin-1-yl)-butyraldehyde with NaBH(OAc)3 in CH2Cl2 gave COMPOUND 153 as a colorless oil. 1H NMR (CDCl3) δ 0.98 (d, 6H, J=6.9 Hz), 1.28-1.46 (m, 4H), 2.19 (s, 3H), 2.28 (s, 3H), 2.53 (dd, 2H, J=7.2, 7.2 Hz), 2.93 (septet, 1H, J=6.9 Hz), 3.05 (t, 2H, J=7.2 Hz), 3.14 (t, 2H, J=7.2 Hz), 3.41 (t, 2H, J=7.2 Hz), 3.72 (s, 4H), 7.14 (dd, 1H, J=7.5, 4.8 Hz), 7.25 (s, 1H), 7.51 (dd, 1H, J=7.5, 1.2 Hz), 8.10 (br s, 1H), 8.19 (s, 1H), 8.33 (dd, 1H, J=4.8, 1.2 Hz); 13C NMR (CDCl3) δ 18.29 (2 carbons), 23.52 (2 carbons), 24.17, 25.51, 27.48, 41.29, 44.36, 48.91, 54.31, 58.75, 59.38, 123.20, 132.28, 133.29, 133.85, 139.13, 144.34, 145.95, 146.48, 154.29, 156.08, 165.16; ES-MS m/z 426 (M+H). Anal. Calcd. For C24H35N5O2.1.2H2O: C, 64.46; H, 8.43; N, 15.66. Found: C, 64.57; H, 8.03; N, 15.28.

Sources & evidence

ORD record
ord-b90c54d6ec214b0bafd1c5d3e8929f7e
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

Loading…