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

HRID 251027Notes

Reaction equation

HRID 251027 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[CH:14]=[C:13]([CH2:15][CH2:16][NH2:17])[N:12]=[CH:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:19][C:20]1[C:21]([CH:27]=O)=[N:22][CH:23]=[C:24]([CH3:26])[CH:25]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:19][C:20]1[C:21]([CH2:27][NH:17][CH2:16][CH2:15][C:13]2[N:12]=[CH:11][N:10]([S:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:18])=[CH:6][CH:5]=3)(=[O:9])=[O:8])[CH:14]=2)=[N:22][CH:23]=[C:24]([CH3:26])[CH:25]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 187316833,5-Dimethylpyridine-2-carbaldehydeHCID 540035372-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethylamine

Product 1

HCID 67273302(3,5-dimethyl-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 2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethylamine and 3,5-dimethyl-pyridine-2-carbaldehyde in CH2Cl2 with NaBH(OAc)3 gave (3,5-dimethyl-pyridin-2-ylmethyl)-{2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethyl}-amine. 1H NMR (CDCl3) δ 2.26 (d, 6H, J=8.65 Hz), 2.44 (s, 3H), 2.78 (t, 2H, J=7.06 Hz), 2.97 (t, 2H, J=7.02 Hz), 3.85 (s, 2H), 7.09 (s, 1H), 7.23 (s, 1H), 7.34 (d, 2H, J=7.84 Hz), 7.81 (d, 2H, J=8.34 Hz), 7.92 (s, 1H), 8.18 (s, 1H).

Sources & evidence

ORD record
ord-23557ff7746a4cd2b86495c16aadbce2
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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