Benzyl Chloride → HCID 71496052, compound

HRID 588056Notes

Reaction equation

HRID 588056 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:23])[C:10]2[CH:15]=[CH:14][CH:13]=[N:12][C:11]=2[NH:16][C@H:17]2[CH2:22][CH2:21][CH2:20][NH:19][CH2:18]2)[CH:5]=[CH:6][CH:7]=1.ClC1C=C(NC(=O)C2C=CC=NC=2NC2CC(C)(C)NC(C)(C)C2)C=CC=1.[CH2:51](Cl)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1.BrCCO>>[CH2:51]([N:19]1[CH2:20][CH2:21][CH2:22][C@@H:17]([NH:16][C:11]2[N:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)=[O:23])[CH2:18]1)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

Participants

5

Reactant 4

HCID 7503Benzyl ChlorideHCID 108982-BromoethanolHCID 71496163HCID 71496163, compoundHCID 71496699HCID 71496699, compound

Product 1

HCID 71496052HCID 71496052, compoundYield 64.4%

Procedure

The title compound was prepared in the same manner as in Example 21, with the exception that (S)—N-(3-chlorophenyl)-2-(3-piperidylamino)nicotinamide of Example 20-A, instead of N-(3-chlorophenyl)-2-(2,2,6,6-tetramethylpiperidin-4-ylamino)nicotinamide, and benzylchloride, instead of 2-bromoethanol, were used in the same molar amounts (Yield: 64.4%). 1H NMR (CDCl3) δ 8.33 (d, 1H), 8.24 (d, 1H), 7.83 (s, 1H), 7.74 (s, 1H), 7.68 (d, 1H), 7.47-7.13 (m, 7H), 6.53-6.46 (m, 1H), 4.39-4.27 (m, 1H), 2.69 (d, 1H), 2.53-2.34 (m, 3H), 1.85-1.58 (m, 6H) ppm.

Sources & evidence

ORD record
ord-0659c7ed79f946008644c11ed9ceee7b
Source dataset
uspto-grants-2016_01
Patent number
US09227955B2

Reaction notes

Loading…