Sodium triacetoxyborohydride → (3,5-Dimethyl-pyridin-2-ylmethyl)-(3,4,5,6-tetrahydro-2h-[1,3']bipyridinyl-2'-ylmethyl)-amine

HRID 251061Notes

Reaction equation

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

Participants

Reactant 3

HCID 5049666Sodium triacetoxyborohydride

HCID 187316833,5-Dimethylpyridine-2-carbaldehyde

HCID 67272595(3-Piperidin-1-yl-2-pyridinyl)methanamine

Product 1

HCID 67272499(3,5-Dimethyl-pyridin-2-ylmethyl)-(3,4,5,6-tetrahydro-2h-[1,3']bipyridinyl-2'-ylmethyl)-amine

Procedure

Using General Procedure B: Reaction of C-(3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-2′-yl)-methylamine, 3,5-dimethyl-pyridine-2-carbaldehyde and NaBH(OAc)3 gave (3,5-dimethyl-pyridin-2-ylmethyl)-(3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-2′-ylmethyl)-amine. 1H NMR (CDCl3) δ 1.50-1.57 (m, 2H), 1.63-1.72 (m, 4H), 2.24 (s, 3H), 2.28 (s, 3H), 2.82 (t, 4H, J=5.1 Hz), 3.91 (s, 2H), 4.01 (s, 2H), 7.07 (dd, 1H, J=4.5, 8.1 Hz), 7.20 (s, 1H), 7.28 (dd, 1H, J=1.2, 8.1 Hz), 8.20 (s, 1H), 8.23 (dd, 1H, J=1.2, 4.5 Hz). Further reaction of (3,5-dimethyl-pyridin-2-ylmethyl)-(3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl-2′-ylmethyl)-amine, 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyraldehyde and NaBH(OAc)3 following General Procedure B gave a colorless oil. Deprotection with NH2NH2.H2O following General Procedure E, and subsequent conversion to the HBr salt, gave COMPOUND 202 as a yellow solid. 1H NMR (CD3OD) δ 1.55-1.83 (m, 10H), 2.51 (s, br. 6H), 2.71-2.76 (m, 2H), 2.922 (t, 2H, J=7.5 Hz), 3.00-3.04 (m, 4H), 4.32 (s, 2H), 4.33 (s, 2H), 7.89 (dd, 1H, J=5.7, 8.4 Hz), 8.20 (d, 1H, J=8.4 Hz), 8.23 (s, 1H), 8.56 (d, 1H, J=5.7 Hz), 8.62 (s, 1H); 13C NMR (D2O) δ 17.20, 17.45, 23.08, 23.45, 25.04, 25.73, 39.68, 52.55, 53.42, 54.35, 56.32, 126.47, 133.78, 135.55, 137.45, 137.74, 147.08, 147.50, 148.70, 150.86. ES-MS m/z 382 (M+H). Anal. Calcd. for C23H35N5O.3.8HBr.0.9H2O.0.3C4H10O: C, 39.96; H, 6.04; N, 9.63; Br, 41.74. Found: C, 39.93; H, 6.08; N, 9.64; Br, 41.68.

Sources & evidence

ORD record: ord-5ef5ba0a72714da29fddbc4c6f99ed3a
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863293B2

Reaction notes

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