Sodium triacetoxyborohydride → 4-[((3,5-Dimethyl-pyridin-2-ylmethyl)-{3-[1-(4-fluoro-phenyl)-1-methyl-ethyl]-pyridin-2-ylmethyl}-amino)-methyl]-3-hydroxymethyl-benzamide

HRID 251261Notes

Reaction equation

HRID 251261 reaction equation
[CH3:1][C:2]1[C:3]([CH2:9][NH:10][CH2:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=2[CH2:20][OH:21])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([C:32]2[C:33]([CH:38]=O)=[N:34][CH:35]=[CH:36][CH:37]=2)([CH3:31])[CH3:30])=[CH:25][CH:24]=1.[BH-](OC(C)=O)(OC(C)=O)[O:41]C(C)=O.[Na+]>C(Cl)Cl>[CH3:1][C:2]1[C:3]([CH2:9][N:10]([CH2:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]([NH2:17])=[O:41])=[CH:14][C:13]=2[CH2:20][OH:21])[CH2:38][C:33]2[C:32]([C:29]([C:26]3[CH:25]=[CH:24][C:23]([F:22])=[CH:28][CH:27]=3)([CH3:31])[CH3:30])=[CH:37][CH:36]=[CH:35][N:34]=2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 672721574-{[(3,5-Dimethyl-pyridin-2-ylmethyl)-amino]-methyl}-3-hydroxymethyl-benzonitrileHCID 865947653-[1-(4-Fluoro-phenyl)-1-methyl-ethyl]pyridine-2-carbaldehyde

Product 1

HCID 589969304-[((3,5-Dimethyl-pyridin-2-ylmethyl)-{3-[1-(4-fluoro-phenyl)-1-methyl-ethyl]-pyridin-2-ylmethyl}-amino)-methyl]-3-hydroxymethyl-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B: Reaction of 4-{[(3,5-dimethyl-pyridin-2-ylmethyl)-amino]-methyl}-3-hydroxymethyl-benzonitrile in CH2Cl2 with 3-[1-(4-fluoro-phenyl)-1-methyl-ethyl]-pyridine-2-carbaldehyde and NaBH(OAc)3 gave 4-[((3,5-dimethyl-pyridin-2-ylmethyl)-{3-[1-(4-fluoro-phenyl)-1-methyl-ethyl]-pyridin-2-ylmethyl}-amino)-methyl]-3-hydroxymethyl-benzamide as a white foam. 1H NMR (CDCl3) δ 1.62 (s, 6H), 2.24 (s, 3H), 2.26 (s, 3H), 3.05 (s, 2H), 3.21 (s, 2H), 3.47 (s, 1H), 3.59 (s, 2H), 4.18 (s, 2H), 5.75 (br s, 1H), 6.29 (br s, 1H), 6.89 (t, 1H, J=9.0 Hz), 7.02 (m, 3H), 7.21 (dd, 1H, J=7.5, 3.0 Hz), 7.26 (s, 1H), 7.61 (d, 1H, J=7.5 Hz), 7.66 (s, 1H), 7.87 (d, 1H, J=7.5 Hz), 8.15 (s, 1H), 8.45 (d, 1H, J=3.0 Hz). 13C NMR (CDCl3) δ 18.3, 18.5, 31.3, 42.3, 51.1, 57.78, 58.4, 58.9, 63.1, 115.6, 115.8, 122.2, 127.1, 127.6, 127.7, 130.3, 131.8, 132.5, 133.5, 133.6, 134.3, 139.5, 141.7, 142.4, 143.5, 145.5, 146.8, 146.9, 152.7, 156.7, 159.9, 163.1, 169.5. HPLC: 98%. ES-MS m/z 527 [M+H]+, 549 [M+Na]+. Anal. Calcd. for C32H35N4O2F.0.4 CH2Cl2: C, 69.41; H, 6.44; N, 9.99. Found: C, 69.15; H, 6.35; N, 9.97.

Sources & evidence

ORD record
ord-d509f11a4e8d4d858bb73b989abb65c9
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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