Ephedrine → HCID 11396843, compound

HRID 1158780Notes

Reaction equation

[C:1]1([C:7]2[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]=[C:9]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24][NH:25][C@@H:26]([CH3:35])[C@@H:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[OH:28]>>[OH:28][CH:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:26]([N:25]([CH3:24])[C:13]([C:12]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][C:9]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[N:10][CH:11]=1)=[O:15])[CH3:35]

Participants

Reactant 2

HCID 9294Ephedrine

HCID 68644304HCID 68644304, compound

Product 1

HCID 11396843HCID 11396843, compoundYield 61.7%

Procedure

Starting from 4-phenyl-2-[(pyridin-2-ylmethyl)amino]pyrimidine-5-carboxylic acid (0.48 g, 1.5 mmol) and (1R,2S)-2-methylamino-1-phenyl-1-propanol [(−)-ephedrine] (0.25 g, 1.5 mmol) according to the method described in Example 17. the title amide 0.42 g (58%) is obtained as white crystalline material; m.p.: 82° C.; [M+H]+ 468.

Sources & evidence

ORD record: ord-1c7906fb02d54ae3b922a6fd3e05f7df
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812031B2

Reaction notes

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