Sodium triacetoxyborohydride → (3,5-dimethyl-pyridin-2-ylmethyl)-(3-isopropyl-pyridin-2-ylmethyl)-{2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethyl}-amine

HRID 251030Notes

Reaction equation

HRID 251030 reaction equation
[CH3:1][C:2]1[C:3]([CH2:9][NH:10][CH2:11][CH2:12][C:13]2[N:14]=[CH:15][N:16]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:17]=2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH:28]([C:31]1[C:32]([CH:37]=O)=[N:33][CH:34]=[CH:35][CH:36]=1)([CH3:30])[CH3:29].[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]([CH2:37][C:32]2[C:31]([CH:28]([CH3:30])[CH3:29])=[CH:36][CH:35]=[CH:34][N:33]=2)[CH2:11][CH2:12][C:13]2[N:14]=[CH:15][N:16]([S:18]([C:21]3[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=3)(=[O:19])=[O:20])[CH:17]=2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 450836353-IsopropylpicolinaldehydeHCID 67273302(3,5-dimethyl-pyridin-2-ylmethyl)-{2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethyl}-amine

Product 1

HCID 67272747(3,5-dimethyl-pyridin-2-ylmethyl)-(3-isopropyl-pyridin-2-ylmethyl)-{2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethyl}-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B: Reaction of (3,5-dimethyl-pyridin-2-ylmethyl)-{2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethyl}-amine and 3-isopropyl-pyridine-2-carbaldehyde in CH2Cl2 (5 mL) with NaBH(OAc)3 gave (3,5-dimethyl-pyridin-2-ylmethyl)-(3-isopropyl-pyridin-2-ylmethyl)-{2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethyl}-amine. 1H NMR (CDCl3) δ 0.91 (d, 6H, J=6.51 Hz), 2.04 (s, 3H), 2.24 (s, 1H), 2.26 (s, 3H), 2.41 (s, 3H), 2.71 (m, 2H), 2.82 (m, 2H), 3.75 (d, 4H, J=4.50 Hz), 6.63 (s, 1H), 7.14 (q, 1H, J=4.25 Hz), 7.22 (s, 1H), 7.30 (d, 2H, 7.86 Hz), 7.49 (d, 1H, J=7.0 Hz), 7.70 (d, 2H, J=8.40 Hz), 7.80 (s, 1H), 8.19 (s, 1H), 8.32 (d, 1H, J=4.19 Hz).

Sources & evidence

ORD record
ord-97025d5717b04624a806dcd645766339
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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