Sodium triacetoxyborohydride → HCID 67272743, compound

HRID 1592509Notes

Reaction equation

HRID 1592509 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][C:14]1[N:18]([CH3:19])[C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[N:15]=1)([CH3:4])([CH3:3])[CH3:2].[BH-](O[C:35]([CH3:37])=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CC1C(C=O)=NC=CC=1>[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:13][C:14]1[N:18]([CH3:19])[C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[N:15]=1)[CH2:14][C:13]1[C:35]([CH3:37])=[CH:9][CH:10]=[CH:11][N:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 67272476{4-[(1-methyl-1H-benzoimidazol-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester

Product 1

HCID 67272743HCID 67272743, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 15018743-Methylpyridine-2-carboxaldehydeSolvent

Procedure

Using General Procedure B, reaction of {4-[(1-methyl-1H-benzoimidazol-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester in CH2Cl2 and 3-methyl-pyridine-2-carbaldehyde in CH2Cl2 with NaBH(OAc)3 gave {4-[(1-methyl-1H-benzoimidazol-2-ylmethyl)-(3-methyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester as a white solid. 1H NMR (CDCl3) δ 1.42 (s, 9H), 1.50-1.60 (m, 2H), 1.78 (s, 2H), 2.27 (s, 3H), 2.60 (t, 2H, J=7.4 Hz), 2.96-3.00 (m, 2H), 3.55 (s, 3H), 3.82 (s, 2H), 3.90 (s, 2H), 4.79-4.80 (m, 1H), 7.09-7.13 (m, 1H), 7.23-7.25 (m, 3H), 7.43 (d, 1H, J=7.4 Hz), 7.70-7.73 (m, 1H), 8.40 (d, 1H, J=4.9 Hz). Deprotection with TFA using General Procedure F gave COMPOUND 226 as a white solid. 1H NMR (CDCl3) δ 1.25-1.34 (m, 4H), 1.50-1.60 (m, 2H), 2.28 (s, 3H), 2.52-2.63 (m, 4H), 3.56 (s, 3H), 3.83 (s, 2H), 3.91 (s, 2H), 7.10-7.14 (m, 1H), 7.22-7.25 (m, 3H), 7.43 (d, 1H, J=7.5 Hz), 7.71-7.73 (m, 1H), 8.41 (d, 1H, J=3.6 Hz). 13C NMR (CDCl3) δ 18.55, 23.95, 29.97, 31.79, 42.19, 51.70, 54.99, 59.43, 109.37, 119.91, 122.15, 122.80, 122.95, 133.34, 136.56, 138.44, 142.55, 146.68, 152.48, 157.02. ES-MS m/z 338 (M+H). Anal. Calcd. for C20H27N5.0.1H2O: C, 70.81; H, 8.08; N, 20.64. Found: C, 70.67; H, 8.02; N, 20.73.

Sources & evidence

ORD record
ord-00144f4f8b194a13bfb91bdf8d97bb67
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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